# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_7
_database_code_depnum_ccdc_archive 'CCDC 1516467'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Ho N4 O9'
_chemical_formula_weight         594.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+5/6'
'-y, x-y, z+2/3'
'-x, -y, z+1/2'
'-x+y, -x, z+1/3'
'y, -x+y, z+1/6'

_cell_length_a                   11.2387(8)
_cell_length_b                   11.2387(8)
_cell_length_c                   26.491(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2897.8(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3872
_cell_measurement_theta_min      2.229
_cell_measurement_theta_max      27.648

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.043
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    4.159
_shelx_estimated_absorpt_T_min   0.359
_shelx_estimated_absorpt_T_max   0.614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.502
_exptl_absorpt_correction_T_max  0.582
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12213
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.229
_diffrn_reflns_theta_max         27.648
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3872
_reflns_number_gt                3774
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.960
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.977

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²+16.2321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3872
_refine_ls_number_parameters     290
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.005

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ho1 Ho -0.14617(4) -0.17205(5) -0.35467(3) 0.01607(14) Uani 1 1 d . . . . .
O1 O -0.2888(10) -0.1850(11) -0.4225(3) 0.030(2) Uani 1 1 d . . . . .
O2 O -0.1807(9) -0.2160(10) -0.4861(4) 0.0263(19) Uani 1 1 d . . . . .
O3 O 0.0637(10) -0.0224(10) -0.3116(4) 0.029(2) Uani 1 1 d . . . . .
O4 O -0.0170(11) 0.0172(10) -0.4040(4) 0.035(2) Uani 1 1 d . . . . .
O5 O -0.0042(10) -0.2399(11) -0.3871(4) 0.029(2) Uani 1 1 d . . . . .
H5B H -0.0584 -0.2968 -0.4071 0.035 Uiso 1 1 calc R U . . .
O6 O -0.1406(11) -0.2887(10) -0.2823(4) 0.031(2) Uani 1 1 d . . . . .
O7 O -0.2884(10) -0.4164(10) -0.3734(4) 0.031(2) Uani 1 1 d . . . . .
O8 O -0.3882(10) -0.3315(10) -0.3302(4) 0.031(2) Uani 1 1 d . . . . .
O9 O -0.4937(13) -0.5494(10) -0.3460(6) 0.060(4) Uani 1 1 d . . . . .
N1 N -0.4444(12) -0.1900(13) -0.5879(5) 0.035(3) Uani 1 1 d . . . . .
N2 N 0.4154(10) 0.1970(13) -0.1889(6) 0.035(2) Uani 1 1 d . U . . .
N3 N 0.4645(15) -0.088(2) -0.3610(7) 0.064(5) Uani 1 1 d . . . . .
N4 N -0.3916(12) -0.4387(12) -0.3490(5) 0.036(3) Uani 1 1 d . . . . .
C1 C -0.3646(12) -0.2066(14) -0.5548(5) 0.025(3) Uani 1 1 d . . . . .
H1A H -0.3049 -0.2355 -0.5660 0.030 Uiso 1 1 calc R U . . .
C2 C -0.3691(12) -0.1821(12) -0.5051(4) 0.021(2) Uani 1 1 d . . . . .
C3 C -0.4635(13) -0.1496(14) -0.4871(6) 0.029(3) Uani 1 1 d . . . . .
H3A H -0.4750 -0.1436 -0.4526 0.034 Uiso 1 1 calc R U . . .
C4 C -0.5413(14) -0.1259(16) -0.5218(6) 0.038(3) Uani 1 1 d . . . . .
H4A H -0.5979 -0.0925 -0.5111 0.045 Uiso 1 1 calc R U . . .
C5 C -0.5344(15) -0.1517(16) -0.5713(7) 0.039(4) Uani 1 1 d . . . . .
H5A H -0.5923 -0.1431 -0.5942 0.047 Uiso 1 1 calc R U . . .
C6 C -0.2712(11) -0.1948(12) -0.4682(4) 0.018(2) Uani 1 1 d . . . . .
C7 C 0.2823(13) 0.1309(15) -0.2054(5) 0.029(3) Uani 1 1 d . . . . .
H7A H 0.2131 0.1039 -0.1814 0.035 Uiso 1 1 calc R U . . .
C8 C 0.2443(13) 0.1020(12) -0.2550(5) 0.023(2) Uani 1 1 d . . . . .
C9 C 0.3492(15) 0.1420(17) -0.2902(6) 0.039(3) Uani 1 1 d . . . . .
H9A H 0.3285 0.1258 -0.3244 0.047 Uiso 1 1 calc R U . . .
C10 C 0.4854(14) 0.2063(18) -0.2742(7) 0.042(4) Uani 1 1 d . . . . .
H10A H 0.5569 0.2337 -0.2973 0.051 Uiso 1 1 calc R U . . .
C11 C 0.5114(17) 0.2285(18) -0.2223(7) 0.045(4) Uani 1 1 d . . . . .
H11A H 0.6018 0.2678 -0.2112 0.054 Uiso 1 1 calc R U . . .
C12 C 0.0963(13) 0.0311(12) -0.2696(5) 0.024(2) Uani 1 1 d . . . . .
C13 C 0.3623(16) -0.1013(19) -0.3870(6) 0.041(4) Uani 1 1 d . . . . .
H13A H 0.3810 -0.0625 -0.4191 0.049 Uiso 1 1 calc R U . . .
C14 C 0.2263(14) -0.1688(11) -0.3714(4) 0.023(3) Uani 1 1 d . . . . .
C15 C 0.1992(16) -0.2199(16) -0.3225(5) 0.034(3) Uani 1 1 d . . . . .
H15A H 0.1110 -0.2612 -0.3091 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3112(19) -0.206(2) -0.2942(7) 0.048(4) Uani 1 1 d . . . . .
H16A H 0.2973 -0.2412 -0.2615 0.057 Uiso 1 1 calc R U . . .
C17 C 0.4352(18) -0.145(2) -0.3137(8) 0.054(5) Uani 1 1 d . . . . .
H17A H 0.5068 -0.1396 -0.2944 0.064 Uiso 1 1 calc R U . . .
C18 C 0.1140(12) -0.1828(12) -0.4055(4) 0.019(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ho1 O2 2.248(9) 6 ?
Ho1 O5 2.254(9) . ?
Ho1 O4 2.292(10) . ?
Ho1 O6 2.342(9) . ?
Ho1 O1 2.364(9) . ?
Ho1 O3 2.393(9) . ?
Ho1 O7 2.440(9) . ?
Ho1 O8 2.481(10) . ?
Ho1 N4 2.889(11) . ?
O1 C6 1.241(14) . ?
O2 C6 1.248(14) . ?
O2 Ho1 2.248(9) 2_554 ?
O3 C12 1.231(16) . ?
O4 C12 1.246(16) 2_554 ?
O5 C18 1.249(15) . ?
O5 H5B 0.8200 . ?
O6 C18 1.232(15) 6 ?
O7 N4 1.239(17) . ?
O8 N4 1.287(16) . ?
O9 N4 1.201(16) . ?
N1 C1 1.332(17) . ?
N1 C5 1.36(2) . ?
N2 C11 1.30(2) . ?
N2 C7 1.367(16) . ?
N3 C13 1.28(2) . ?
N3 C17 1.37(3) . ?
C1 C2 1.349(18) . ?
C1 H1A 0.9300 . ?
C2 C3 1.371(17) . ?
C2 C6 1.530(16) . ?
C3 C4 1.382(19) . ?
C3 H3A 0.9300 . ?
C4 C5 1.35(2) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C7 C8 1.371(18) . ?
C7 H7A 0.9300 . ?
C8 C9 1.390(19) . ?
C8 C12 1.491(17) . ?
C9 C10 1.39(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.40(2) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O4 1.245(16) 6 ?
C13 C14 1.39(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.386(18) . ?
C14 C18 1.495(16) . ?
C15 C16 1.41(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.31(3) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 O6 1.231(15) 2_554 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Ho1 O5 159.6(4) 6 . ?
O2 Ho1 O4 83.0(4) 6 . ?
O5 Ho1 O4 82.5(4) . . ?
O2 Ho1 O6 99.1(3) 6 . ?
O5 Ho1 O6 84.3(3) . . ?
O4 Ho1 O6 143.6(4) . . ?
O2 Ho1 O1 84.2(3) 6 . ?
O5 Ho1 O1 105.2(3) . . ?
O4 Ho1 O1 73.7(4) . . ?
O6 Ho1 O1 142.7(4) . . ?
O2 Ho1 O3 83.1(4) 6 . ?
O5 Ho1 O3 78.7(3) . . ?
O4 Ho1 O3 71.0(3) . . ?
O6 Ho1 O3 73.1(4) . . ?
O1 Ho1 O3 143.6(4) . . ?
O2 Ho1 O7 126.7(3) 6 . ?
O5 Ho1 O7 73.6(3) . . ?
O4 Ho1 O7 133.1(4) . . ?
O6 Ho1 O7 73.9(4) . . ?
O1 Ho1 O7 74.6(3) . . ?
O3 Ho1 O7 138.5(3) . . ?
O2 Ho1 O8 75.7(3) 6 . ?
O5 Ho1 O8 124.1(4) . . ?
O4 Ho1 O8 140.9(4) . . ?
O6 Ho1 O8 73.1(4) . . ?
O1 Ho1 O8 71.9(3) . . ?
O3 Ho1 O8 136.3(3) . . ?
O7 Ho1 O8 51.4(3) . . ?
O2 Ho1 N4 102.0(4) 6 . ?
O5 Ho1 N4 98.0(4) . . ?
O4 Ho1 N4 145.7(4) . . ?
O6 Ho1 N4 69.8(4) . . ?
O1 Ho1 N4 73.1(4) . . ?
O3 Ho1 N4 143.0(4) . . ?
O7 Ho1 N4 25.1(4) . . ?
O8 Ho1 N4 26.3(3) . . ?
C6 O1 Ho1 127.9(8) . . ?
C6 O2 Ho1 152.7(9) . 2_554 ?
C12 O3 Ho1 136.3(9) . . ?
C12 O4 Ho1 162.3(10) 2_554 . ?
C18 O5 Ho1 136.5(9) . . ?
C18 O5 H5B 109.5 . . ?
Ho1 O5 H5B 97.8 . . ?
C18 O6 Ho1 133.6(8) 6 . ?
N4 O7 Ho1 98.2(8) . . ?
N4 O8 Ho1 94.8(7) . . ?
C1 N1 C5 119.4(13) . . ?
C11 N2 C7 117.7(14) . . ?
C13 N3 C17 116.5(15) . . ?
O9 N4 O7 123.9(14) . . ?
O9 N4 O8 120.7(14) . . ?
O7 N4 O8 115.2(11) . . ?
O9 N4 Ho1 179.2(13) . . ?
O7 N4 Ho1 56.7(6) . . ?
O8 N4 Ho1 58.8(6) . . ?
N1 C1 C2 121.2(13) . . ?
N1 C1 H1A 119.4 . . ?
C2 C1 H1A 119.4 . . ?
C1 C2 C3 120.5(12) . . ?
C1 C2 C6 120.1(11) . . ?
C3 C2 C6 119.4(11) . . ?
C2 C3 C4 117.9(13) . . ?
C2 C3 H3A 121.0 . . ?
C4 C3 H3A 121.1 . . ?
C5 C4 C3 119.6(13) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 N1 120.9(13) . . ?
C4 C5 H5A 119.5 . . ?
N1 C5 H5A 119.5 . . ?
O1 C6 O2 124.7(11) . . ?
O1 C6 C2 117.5(10) . . ?
O2 C6 C2 117.9(10) . . ?
C8 C7 N2 124.2(13) . . ?
C8 C7 H7A 117.9 . . ?
N2 C7 H7A 117.9 . . ?
C7 C8 C9 117.0(12) . . ?
C7 C8 C12 120.4(11) . . ?
C9 C8 C12 122.6(12) . . ?
C10 C9 C8 119.9(14) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.1 . . ?
C11 C10 C9 117.9(14) . . ?
C11 C10 H10A 121.0 . . ?
C9 C10 H10A 121.0 . . ?
N2 C11 C10 123.2(15) . . ?
N2 C11 H11A 118.4 . . ?
C10 C11 H11A 118.4 . . ?
O4 C12 O3 126.3(12) 6 . ?
O4 C12 C8 115.4(12) 6 . ?
O3 C12 C8 118.3(11) . . ?
N3 C13 C14 125.5(16) . . ?
N3 C13 H13A 117.3 . . ?
C14 C13 H13A 117.3 . . ?
C15 C14 C13 117.4(13) . . ?
C15 C14 C18 121.4(13) . . ?
C13 C14 C18 121.2(11) . . ?
C14 C15 C16 117.0(14) . . ?
C14 C15 H15A 121.5 . . ?
C16 C15 H15A 121.5 . . ?
C17 C16 C15 120.2(17) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 N3 123.3(16) . . ?
C16 C17 H17A 118.3 . . ?
N3 C17 H17A 118.3 . . ?
O6 C18 O5 127.4(11) 2_554 . ?
O6 C18 C14 116.1(11) 2_554 . ?
O5 C18 C14 116.4(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ho1 O7 N4 O9 -179.3(15) . . . . ?
Ho1 O7 N4 O8 6.9(13) . . . . ?
Ho1 O8 N4 O9 179.3(14) . . . . ?
Ho1 O8 N4 O7 -6.7(13) . . . . ?
C5 N1 C1 C2 -2(2) . . . . ?
N1 C1 C2 C3 5(2) . . . . ?
N1 C1 C2 C6 -176.9(12) . . . . ?
C1 C2 C3 C4 -8(2) . . . . ?
C6 C2 C3 C4 173.9(13) . . . . ?
C2 C3 C4 C5 8(2) . . . . ?
C3 C4 C5 N1 -5(2) . . . . ?
C1 N1 C5 C4 2(2) . . . . ?
Ho1 O1 C6 O2 9.0(19) . . . . ?
Ho1 O1 C6 C2 -172.0(8) . . . . ?
Ho1 O2 C6 O1 -98(2) 2_554 . . . ?
Ho1 O2 C6 C2 83(2) 2_554 . . . ?
C1 C2 C6 O1 -172.8(12) . . . . ?
C3 C2 C6 O1 5.3(18) . . . . ?
C1 C2 C6 O2 6.2(18) . . . . ?
C3 C2 C6 O2 -175.6(12) . . . . ?
C11 N2 C7 C8 -3(2) . . . . ?
N2 C7 C8 C9 1(2) . . . . ?
N2 C7 C8 C12 -179.2(13) . . . . ?
C7 C8 C9 C10 1(2) . . . . ?
C12 C8 C9 C10 -179.2(14) . . . . ?
C8 C9 C10 C11 0(3) . . . . ?
C7 N2 C11 C10 4(3) . . . . ?
C9 C10 C11 N2 -3(3) . . . . ?
Ho1 O3 C12 O4 -11(2) . . . 6 ?
Ho1 O3 C12 C8 170.3(8) . . . . ?
C7 C8 C12 O4 18.4(17) . . . 6 ?
C9 C8 C12 O4 -161.5(14) . . . 6 ?
C7 C8 C12 O3 -162.8(13) . . . . ?
C9 C8 C12 O3 17(2) . . . . ?
C17 N3 C13 C14 0(3) . . . . ?
N3 C13 C14 C15 4(3) . . . . ?
N3 C13 C14 C18 -177.8(17) . . . . ?
C13 C14 C15 C16 -4(2) . . . . ?
C18 C14 C15 C16 177.5(14) . . . . ?
C14 C15 C16 C17 2(3) . . . . ?
C15 C16 C17 N3 2(3) . . . . ?
C13 N3 C17 C16 -2(3) . . . . ?
Ho1 O5 C18 O6 -81.8(17) . . . 2_554 ?
Ho1 O5 C18 C14 100.7(13) . . . . ?
C15 C14 C18 O6 -176.2(12) . . . 2_554 ?
C13 C14 C18 O6 5.3(19) . . . 2_554 ?
C15 C14 C18 O5 1.6(18) . . . . ?
C13 C14 C18 O5 -176.9(13) . . . . ?

_refine_diff_density_max         1.505
_refine_diff_density_min         -1.516
_refine_diff_density_rms         0.166

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1516461'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 Eu2 N3 O15'
_chemical_formula_weight         853.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8972(9)
_cell_length_b                   17.0855(16)
_cell_length_c                   15.2347(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.039(4)
_cell_angle_gamma                90
_cell_volume                     2264.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3935
_cell_measurement_theta_min      2.983
_cell_measurement_theta_max      24.997

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.502
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    5.580
_shelx_estimated_absorpt_T_min   0.277
_shelx_estimated_absorpt_T_max   0.304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.210
_exptl_absorpt_correction_T_max  0.222
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11407
_diffrn_reflns_av_unetI/netI     0.1704
_diffrn_reflns_av_R_equivalents  0.1514
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.983
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3935
_reflns_number_gt                2298
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3935
_refine_ls_number_parameters     370
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.1523
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.36230(10) 0.08584(5) 0.92595(6) 0.0116(2) Uani 1 1 d . . . . .
Eu2 Eu 0.16099(10) 0.14823(5) 1.13058(6) 0.0098(2) Uani 1 1 d . . . . .
O1 O 0.2918(12) 0.2184(7) 0.8927(8) 0.010(3) Uani 1 1 d . U . . .
O2 O 0.2337(13) 0.2480(7) 1.2478(8) 0.011(3) Uani 1 1 d . U . . .
O3 O 0.1576(15) 0.2665(8) 1.0497(9) 0.024(3) Uani 1 1 d . U . . .
O4 O 0.3801(17) 0.3291(9) 1.0707(10) 0.039(4) Uani 1 1 d . U . . .
O5 O 0.2091(13) 0.0062(7) 1.1311(8) 0.016(3) Uani 1 1 d . U . . .
O6 O 0.6026(13) 0.0127(7) 0.9464(8) 0.011(3) Uani 1 1 d . U . . .
O7 O 0.0677(13) 0.0998(7) 0.8307(8) 0.016(3) Uani 1 1 d . . . . .
O8 O 0.1206(13) 0.1029(7) 0.9783(8) 0.013(3) Uani 1 1 d . . . . .
O9 O -0.0720(13) 0.0708(7) 1.1059(8) 0.013(3) Uani 1 1 d . U . . .
O10 O 0.3020(12) -0.0419(7) 0.8676(8) 0.012(3) Uani 1 1 d . U . . .
O11 O 0.4418(14) 0.1372(8) 1.2141(8) 0.022(3) Uani 1 1 d . . . . .
O12 O 0.4153(13) 0.1518(7) 1.0691(8) 0.014(3) Uani 1 1 d . . . . .
O13 O 0.3754(14) 0.0983(7) 0.7697(8) 0.022(3) Uani 1 1 d . . . . .
H13A H 0.3490 0.0553 0.7429 0.033 Uiso 1 1 d R U . . .
H13B H 0.3145 0.1343 0.7458 0.033 Uiso 1 1 d R U . . .
OW1 O 0.570(3) 0.4279(13) 1.0060(14) 0.095(8) Uani 1 1 d . . . . .
HW1A H 0.5573 0.4406 1.0579 0.143 Uiso 1 1 d R U . . .
HW1B H 0.6647 0.4319 1.0043 0.143 Uiso 1 1 d R U . . .
OW2 O 0.400(3) -0.0267(11) 0.6652(12) 0.110(11) Uani 1 1 d . . . . .
HW2A H 0.3663 -0.0734 0.6645 0.164 Uiso 1 1 d R U . . .
HW2B H 0.3454 -0.0010 0.6221 0.164 Uiso 1 1 d R U . . .
N1 N 0.1401(15) 0.1050(8) 1.2873(9) 0.010(3) Uani 1 1 d . U . . .
N2 N 0.6159(15) 0.1644(8) 0.9235(9) 0.010(3) Uani 1 1 d . U . . .
N3 N -0.0915(15) 0.2184(8) 1.1550(9) 0.010(3) Uani 1 1 d . U . . .
C1 C 0.1931(18) 0.1555(10) 1.3566(11) 0.008(4) Uani 1 1 d . U . . .
C2 C 0.194(2) 0.1340(10) 1.4464(12) 0.015(4) Uani 1 1 d . U . . .
C3 C 0.145(2) 0.0589(11) 1.4633(14) 0.021(5) Uani 1 1 d . U . . .
H3B H 0.1485 0.0414 1.5229 0.025 Uiso 1 1 calc R U . . .
C4 C 0.090(2) 0.0094(12) 1.3886(13) 0.024(5) Uani 1 1 d . . . . .
H4A H 0.0536 -0.0416 1.3976 0.029 Uiso 1 1 calc R U . . .
C5 C 0.091(2) 0.0349(11) 1.3051(12) 0.017(4) Uani 1 1 d . . . . .
H5B H 0.0537 0.0006 1.2562 0.020 Uiso 1 1 calc R U . . .
C6 C 0.241(2) 0.2336(11) 1.3308(13) 0.016(4) Uani 1 1 d . U . . .
C7 C 0.248(2) 0.3145(11) 1.0280(12) 0.016(4) Uani 1 1 d . U . . .
C8 C 0.737(2) 0.1221(11) 0.9105(13) 0.019(4) Uani 1 1 d . U . . .
C9 C -0.1217(19) 0.1562(11) 0.9068(13) 0.017(4) Uani 1 1 d . . . . .
C10 C -0.112(2) 0.2370(11) 0.9061(12) 0.019(5) Uani 1 1 d . . . . .
H10A H -0.0211 0.2624 0.8977 0.029 Uiso 1 1 calc R U . . .
C11 C 0.761(2) 0.2806(12) 0.9178(13) 0.020(4) Uani 1 1 d . U . . .
H11A H 0.7648 0.3361 0.9192 0.030 Uiso 1 1 calc R U . . .
C12 C 0.629(3) 0.2420(12) 0.9275(15) 0.033(6) Uani 1 1 d . . . . .
H12A H 0.5445 0.2720 0.9374 0.039 Uiso 1 1 calc R U . . .
C13 C 0.711(2) 0.0363(11) 0.9097(12) 0.015(4) Uani 1 1 d . U . . .
C14 C 0.026(2) 0.1139(11) 0.9018(12) 0.013(4) Uani 1 1 d . U . . .
C15 C 0.216(2) -0.1715(11) 0.8517(13) 0.017(4) Uani 1 1 d . U . . .
C16 C 0.3555(19) -0.2020(10) 0.8352(12) 0.012(4) Uani 1 1 d . U . . .
C17 C 0.363(2) -0.2804(11) 0.8100(13) 0.021(5) Uani 1 1 d . . . . .
H17A H 0.4529 -0.3022 0.7958 0.031 Uiso 1 1 calc R U . . .
C18 C -0.231(2) 0.3246(11) 1.1930(13) 0.022(5) Uani 1 1 d . . . . .
H18A H -0.2311 0.3783 1.2092 0.033 Uiso 1 1 calc R U . . .
C19 C -0.101(2) 0.2924(11) 1.1732(12) 0.014(4) Uani 1 1 d . . . . .
H19A H -0.0146 0.3251 1.1727 0.017 Uiso 1 1 calc R U . . .
C20 C 0.1952(16) -0.0886(10) 0.8728(10) 0.004(3) Uani 1 1 d . U . . .
C21 C 0.4966(19) 0.1573(10) 1.1497(12) 0.011(4) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O10 2.376(12) . ?
Eu1 O1 2.377(11) . ?
Eu1 O12 2.412(12) . ?
Eu1 O13 2.417(13) . ?
Eu1 O6 2.439(11) . ?
Eu1 O8 2.462(12) . ?
Eu1 O6 2.542(12) 3_657 ?
Eu1 N2 2.633(14) . ?
Eu1 O7 2.728(12) . ?
Eu1 C14 2.974(17) . ?
Eu1 Eu2 4.0487(13) . ?
Eu1 Eu1 4.1703(18) 3_657 ?
Eu1 H13A 2.8152 . ?
Eu1 H13B 2.8134 . ?
Eu2 O3 2.364(13) . ?
Eu2 O8 2.400(11) . ?
Eu2 O9 2.421(12) . ?
Eu2 O2 2.456(11) . ?
Eu2 O5 2.464(12) . ?
Eu2 N1 2.542(14) . ?
Eu2 O11 2.563(12) . ?
Eu2 O12 2.624(12) . ?
Eu2 N3 2.640(14) . ?
Eu2 C21 2.943(17) . ?
O1 C6 1.26(2) 4_565 ?
O2 C6 1.28(2) . ?
O3 C7 1.24(2) . ?
O4 C7 1.24(2) . ?
O5 C13 1.26(2) 3_657 ?
O6 C13 1.28(2) . ?
O6 Eu1 2.542(12) 3_657 ?
O7 C14 1.24(2) . ?
O8 C14 1.30(2) . ?
O9 C20 1.245(18) 3_557 ?
O10 C20 1.256(19) . ?
O11 C21 1.23(2) . ?
O12 C21 1.293(19) . ?
O13 H13A 0.8500 . ?
O13 H13B 0.8501 . ?
OW1 HW1A 0.8500 . ?
OW1 HW1B 0.8500 . ?
OW2 HW2A 0.8499 . ?
OW2 HW2B 0.8501 . ?
N1 C5 1.32(2) . ?
N1 C1 1.37(2) . ?
N2 C12 1.33(2) . ?
N2 C8 1.35(2) . ?
N3 C19 1.30(2) . ?
N3 C15 1.35(2) 3_557 ?
C1 C2 1.42(2) . ?
C1 C6 1.48(2) . ?
C2 C3 1.40(3) . ?
C2 C7 1.52(2) 4_566 ?
C3 C4 1.42(3) . ?
C3 H3B 0.9500 . ?
C4 C5 1.35(3) . ?
C4 H4A 0.9500 . ?
C5 H5B 0.9500 . ?
C6 O1 1.26(2) 4_566 ?
C7 C2 1.52(2) 4_565 ?
C8 C9 1.39(2) 1_655 ?
C8 C13 1.48(3) . ?
C9 C10 1.38(3) . ?
C9 C8 1.39(2) 1_455 ?
C9 C14 1.52(2) . ?
C10 C11 1.40(3) 1_455 ?
C10 H10A 0.9500 . ?
C11 C12 1.38(3) . ?
C11 C10 1.40(3) 1_655 ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 O5 1.26(2) 3_657 ?
C15 N3 1.35(2) 3_557 ?
C15 C16 1.42(2) . ?
C15 C20 1.47(2) . ?
C16 C17 1.40(2) . ?
C16 C21 1.50(2) 3_657 ?
C17 C18 1.38(3) 3_557 ?
C17 H17A 0.9500 . ?
C18 C19 1.37(2) . ?
C18 C17 1.38(3) 3_557 ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 O9 1.245(18) 3_557 ?
C21 C16 1.50(2) 3_657 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O10 Eu1 O1 140.1(4) . . ?
O10 Eu1 O12 138.9(4) . . ?
O1 Eu1 O12 75.0(4) . . ?
O10 Eu1 O13 76.5(4) . . ?
O1 Eu1 O13 76.8(4) . . ?
O12 Eu1 O13 144.0(4) . . ?
O10 Eu1 O6 72.6(4) . . ?
O1 Eu1 O6 134.5(4) . . ?
O12 Eu1 O6 97.1(4) . . ?
O13 Eu1 O6 87.1(4) . . ?
O10 Eu1 O8 94.9(4) . . ?
O1 Eu1 O8 75.3(4) . . ?
O12 Eu1 O8 70.8(4) . . ?
O13 Eu1 O8 122.2(4) . . ?
O6 Eu1 O8 145.2(4) . . ?
O10 Eu1 O6 70.1(4) . 3_657 ?
O1 Eu1 O6 141.2(4) . 3_657 ?
O12 Eu1 O6 69.4(4) . 3_657 ?
O13 Eu1 O6 142.0(4) . 3_657 ?
O6 Eu1 O6 66.3(5) . 3_657 ?
O8 Eu1 O6 78.9(4) . 3_657 ?
O10 Eu1 N2 126.2(4) . . ?
O1 Eu1 N2 72.5(4) . . ?
O12 Eu1 N2 76.6(4) . . ?
O13 Eu1 N2 74.0(4) . . ?
O6 Eu1 N2 62.1(4) . . ?
O8 Eu1 N2 138.9(4) . . ?
O6 Eu1 N2 112.3(4) 3_657 . ?
O10 Eu1 O7 76.4(4) . . ?
O1 Eu1 O7 67.8(4) . . ?
O12 Eu1 O7 115.1(4) . . ?
O13 Eu1 O7 72.9(4) . . ?
O6 Eu1 O7 146.3(4) . . ?
O8 Eu1 O7 49.8(4) . . ?
O6 Eu1 O7 114.6(4) 3_657 . ?
N2 Eu1 O7 132.8(4) . . ?
O10 Eu1 C14 87.6(4) . . ?
O1 Eu1 C14 66.8(4) . . ?
O12 Eu1 C14 92.2(4) . . ?
O13 Eu1 C14 96.7(5) . . ?
O6 Eu1 C14 158.4(4) . . ?
O8 Eu1 C14 25.5(4) . . ?
O6 Eu1 C14 99.3(4) 3_657 . ?
N2 Eu1 C14 139.3(5) . . ?
O7 Eu1 C14 24.6(4) . . ?
O10 Eu1 Eu2 115.4(3) . . ?
O1 Eu1 Eu2 76.9(3) . . ?
O12 Eu1 Eu2 38.3(3) . . ?
O13 Eu1 Eu2 148.8(3) . . ?
O6 Eu1 Eu2 123.6(3) . . ?
O8 Eu1 Eu2 33.2(3) . . ?
O6 Eu1 Eu2 65.7(3) 3_657 . ?
N2 Eu1 Eu2 113.2(3) . . ?
O7 Eu1 Eu2 81.7(3) . . ?
C14 Eu1 Eu2 57.2(4) . . ?
O10 Eu1 Eu1 67.5(3) . 3_657 ?
O1 Eu1 Eu1 152.2(3) . 3_657 ?
O12 Eu1 Eu1 81.8(3) . 3_657 ?
O13 Eu1 Eu1 116.8(3) . 3_657 ?
O6 Eu1 Eu1 33.9(3) . 3_657 ?
O8 Eu1 Eu1 111.3(3) . 3_657 ?
O6 Eu1 Eu1 32.4(3) 3_657 3_657 ?
N2 Eu1 Eu1 87.6(3) . 3_657 ?
O7 Eu1 Eu1 137.7(3) . 3_657 ?
C14 Eu1 Eu1 130.0(4) . 3_657 ?
Eu2 Eu1 Eu1 94.18(3) . 3_657 ?
O10 Eu1 H13A 59.9 . . ?
O1 Eu1 H13A 90.6 . . ?
O12 Eu1 H13A 160.4 . . ?
O13 Eu1 H13A 16.6 . . ?
O6 Eu1 H13A 83.5 . . ?
O8 Eu1 H13A 118.9 . . ?
O6 Eu1 H13A 127.4 3_657 . ?
N2 Eu1 H13A 86.6 . . ?
O7 Eu1 H13A 69.7 . . ?
C14 Eu1 H13A 94.2 . . ?
Eu2 Eu1 H13A 151.4 . . ?
Eu1 Eu1 H13A 107.7 3_657 . ?
O10 Eu1 H13B 85.9 . . ?
O1 Eu1 H13B 62.1 . . ?
O12 Eu1 H13B 134.9 . . ?
O13 Eu1 H13B 16.6 . . ?
O6 Eu1 H13B 103.0 . . ?
O8 Eu1 H13B 108.5 . . ?
O6 Eu1 H13B 155.6 3_657 . ?
N2 Eu1 H13B 78.0 . . ?
O7 Eu1 H13B 61.5 . . ?
C14 Eu1 H13B 83.6 . . ?
Eu2 Eu1 H13B 132.3 . . ?
Eu1 Eu1 H13B 133.4 3_657 . ?
H13A Eu1 H13B 28.6 . . ?
O3 Eu2 O8 77.8(4) . . ?
O3 Eu2 O9 117.9(4) . . ?
O8 Eu2 O9 73.9(4) . . ?
O3 Eu2 O2 76.0(4) . . ?
O8 Eu2 O2 152.9(4) . . ?
O9 Eu2 O2 125.4(4) . . ?
O3 Eu2 O5 145.8(4) . . ?
O8 Eu2 O5 71.1(4) . . ?
O9 Eu2 O5 66.7(4) . . ?
O2 Eu2 O5 131.5(4) . . ?
O3 Eu2 N1 137.9(4) . . ?
O8 Eu2 N1 142.0(4) . . ?
O9 Eu2 N1 76.1(4) . . ?
O2 Eu2 N1 65.1(4) . . ?
O5 Eu2 N1 76.0(4) . . ?
O3 Eu2 O11 103.1(4) . . ?
O8 Eu2 O11 113.0(4) . . ?
O9 Eu2 O11 138.7(4) . . ?
O2 Eu2 O11 67.0(4) . . ?
O5 Eu2 O11 77.0(4) . . ?
N1 Eu2 O11 76.5(4) . . ?
O3 Eu2 O12 73.3(4) . . ?
O8 Eu2 O12 68.2(4) . . ?
O9 Eu2 O12 137.0(4) . . ?
O2 Eu2 O12 97.3(4) . . ?
O5 Eu2 O12 82.1(4) . . ?
N1 Eu2 O12 125.4(4) . . ?
O11 Eu2 O12 49.8(4) . . ?
O3 Eu2 N3 76.5(4) . . ?
O8 Eu2 N3 108.8(4) . . ?
O9 Eu2 N3 62.9(4) . . ?
O2 Eu2 N3 71.6(4) . . ?
O5 Eu2 N3 126.8(4) . . ?
N1 Eu2 N3 76.6(4) . . ?
O11 Eu2 N3 137.2(4) . . ?
O12 Eu2 N3 149.6(4) . . ?
O3 Eu2 C21 84.8(5) . . ?
O8 Eu2 C21 93.3(4) . . ?
O9 Eu2 C21 149.6(4) . . ?
O2 Eu2 C21 77.5(4) . . ?
O5 Eu2 C21 83.1(4) . . ?
N1 Eu2 C21 101.2(5) . . ?
O11 Eu2 C21 24.6(4) . . ?
O12 Eu2 C21 26.1(4) . . ?
N3 Eu2 C21 146.9(5) . . ?
O3 Eu2 Eu1 77.5(3) . . ?
O8 Eu2 Eu1 34.1(3) . . ?
O9 Eu2 Eu1 103.8(3) . . ?
O2 Eu2 Eu1 130.6(3) . . ?
O5 Eu2 Eu1 68.8(3) . . ?
N1 Eu2 Eu1 141.0(3) . . ?
O11 Eu2 Eu1 79.7(3) . . ?
O12 Eu2 Eu1 34.7(3) . . ?
N3 Eu2 Eu1 139.0(3) . . ?
C21 Eu2 Eu1 59.2(3) . . ?
C6 O1 Eu1 144.8(12) 4_565 . ?
C6 O2 Eu2 122.5(11) . . ?
C7 O3 Eu2 139.9(12) . . ?
C13 O5 Eu2 132.7(12) 3_657 . ?
C13 O6 Eu1 120.3(11) . . ?
C13 O6 Eu1 124.1(11) . 3_657 ?
Eu1 O6 Eu1 113.7(5) . 3_657 ?
C14 O7 Eu1 88.9(10) . . ?
C14 O8 Eu2 139.4(11) . . ?
C14 O8 Eu1 99.8(10) . . ?
Eu2 O8 Eu1 112.7(4) . . ?
C20 O9 Eu2 126.8(10) 3_557 . ?
C20 O10 Eu1 132.5(11) . . ?
C21 O11 Eu2 95.2(10) . . ?
C21 O12 Eu1 149.1(11) . . ?
C21 O12 Eu2 90.9(10) . . ?
Eu1 O12 Eu2 106.9(4) . . ?
Eu1 O13 H13A 109.4 . . ?
Eu1 O13 H13B 109.2 . . ?
H13A O13 H13B 109.5 . . ?
HW1A OW1 HW1B 109.5 . . ?
HW2A OW2 HW2B 109.5 . . ?
C5 N1 C1 119.2(16) . . ?
C5 N1 Eu2 123.2(12) . . ?
C1 N1 Eu2 117.4(11) . . ?
C12 N2 C8 118.3(16) . . ?
C12 N2 Eu1 125.2(13) . . ?
C8 N2 Eu1 116.3(11) . . ?
C19 N3 C15 120.3(16) . 3_557 ?
C19 N3 Eu2 124.4(11) . . ?
C15 N3 Eu2 115.3(11) 3_557 . ?
N1 C1 C2 120.9(16) . . ?
N1 C1 C6 115.9(15) . . ?
C2 C1 C6 123.2(16) . . ?
C3 C2 C1 118.6(17) . . ?
C3 C2 C7 116.1(17) . 4_566 ?
C1 C2 C7 125.3(16) . 4_566 ?
C2 C3 C4 117.8(19) . . ?
C2 C3 H3B 121.1 . . ?
C4 C3 H3B 121.1 . . ?
C5 C4 C3 119.8(19) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
N1 C5 C4 123.6(19) . . ?
N1 C5 H5B 118.2 . . ?
C4 C5 H5B 118.2 . . ?
O1 C6 O2 123.5(17) 4_566 . ?
O1 C6 C1 117.9(16) 4_566 . ?
O2 C6 C1 118.6(16) . . ?
O3 C7 O4 126.0(19) . . ?
O3 C7 C2 119.2(16) . 4_565 ?
O4 C7 C2 114.6(17) . 4_565 ?
N2 C8 C9 122.4(17) . 1_655 ?
N2 C8 C13 113.7(16) . . ?
C9 C8 C13 123.7(17) 1_655 . ?
C10 C9 C8 118.4(17) . 1_455 ?
C10 C9 C14 114.8(16) . . ?
C8 C9 C14 126.8(17) 1_455 . ?
C9 C10 C11 118.5(18) . 1_455 ?
C9 C10 H10A 120.7 . . ?
C11 C10 H10A 120.7 1_455 . ?
C12 C11 C10 119.2(19) . 1_655 ?
C12 C11 H11A 120.4 . . ?
C10 C11 H11A 120.4 1_655 . ?
N2 C12 C11 122.9(19) . . ?
N2 C12 H12A 118.6 . . ?
C11 C12 H12A 118.6 . . ?
O5 C13 O6 125.9(17) 3_657 . ?
O5 C13 C8 117.8(17) 3_657 . ?
O6 C13 C8 116.1(16) . . ?
O7 C14 O8 120.1(16) . . ?
O7 C14 C9 123.8(16) . . ?
O8 C14 C9 115.3(16) . . ?
O7 C14 Eu1 66.5(10) . . ?
O8 C14 Eu1 54.7(8) . . ?
C9 C14 Eu1 158.5(12) . . ?
N3 C15 C16 120.1(16) 3_557 . ?
N3 C15 C20 116.7(16) 3_557 . ?
C16 C15 C20 123.2(16) . . ?
C17 C16 C15 119.5(17) . . ?
C17 C16 C21 116.3(16) . 3_657 ?
C15 C16 C21 124.0(16) . 3_657 ?
C18 C17 C16 116.3(18) 3_557 . ?
C18 C17 H17A 121.8 3_557 . ?
C16 C17 H17A 121.8 . . ?
C19 C18 C17 121.4(18) . 3_557 ?
C19 C18 H18A 119.3 . . ?
C17 C18 H18A 119.3 3_557 . ?
N3 C19 C18 122.0(17) . . ?
N3 C19 H19A 119.0 . . ?
C18 C19 H19A 119.0 . . ?
O9 C20 O10 125.5(15) 3_557 . ?
O9 C20 C15 116.7(15) 3_557 . ?
O10 C20 C15 117.8(14) . . ?
O11 C21 O12 120.0(16) . . ?
O11 C21 C16 120.1(15) . 3_657 ?
O12 C21 C16 118.8(15) . 3_657 ?
O11 C21 Eu2 60.1(9) . . ?
O12 C21 Eu2 63.0(8) . . ?
C16 C21 Eu2 152.0(12) 3_657 . ?

_refine_diff_density_max         1.753
_refine_diff_density_min         -2.568
_refine_diff_density_rms         0.408

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1516463'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N4 O9 Sm'
_chemical_formula_weight         579.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'

_cell_length_a                   11.3026(9)
_cell_length_b                   11.3026(9)
_cell_length_c                   26.661(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2949.6(7)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3104
_cell_measurement_theta_min      3.096
_cell_measurement_theta_max      25.354

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_F_000             1698
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    3.048
_shelx_estimated_absorpt_T_min   0.354
_shelx_estimated_absorpt_T_max   0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_T_max  0.673
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8514
_diffrn_reflns_av_unetI/netI     0.1190
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.096
_diffrn_reflns_theta_max         25.354
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3104
_reflns_number_gt                2495
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3104
_refine_ls_number_parameters     290
_refine_ls_number_restraints     93
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.2062
_refine_ls_wR_factor_gt          0.1934
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_restrained_S_all      1.234
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm -0.14397(12) 0.02647(12) 0.22387(10) 0.0220(4) Uani 1 1 d . . . . .
O1 O -0.292(2) -0.110(2) 0.1560(9) 0.040(6) Uani 1 1 d . . . . .
O2 O -0.1826(19) 0.031(2) 0.0935(8) 0.030(5) Uani 1 1 d . . . . .
H2B H -0.1293 0.0190 0.0765 0.036 Uiso 1 1 calc R U . . .
O3 O -0.134(2) 0.157(2) 0.2967(9) 0.047(6) Uani 1 1 d . . . . .
O4 O 0.004(2) 0.2415(19) 0.1911(9) 0.036(5) Uani 1 1 d . U . . .
O5 O -0.014(2) -0.036(2) 0.1745(8) 0.036(5) Uani 1 1 d . U . . .
O6 O 0.0734(19) 0.087(2) 0.2677(8) 0.035(5) Uani 1 1 d . . . . .
O7 O -0.387(2) -0.049(2) 0.2481(9) 0.042(6) Uani 1 1 d . . . . .
O8 O -0.2900(19) 0.132(2) 0.2035(8) 0.029(5) Uani 1 1 d . . . . .
O9 O -0.491(2) 0.062(2) 0.2329(11) 0.049(6) Uani 1 1 d . U . . .
N1 N -0.442(3) -0.253(3) -0.0088(12) 0.045(7) Uani 1 1 d . . . . .
N2 N -0.195(5) 0.328(4) 0.4505(18) 0.086(13) Uani 1 1 d . U . . .
N3 N 0.224(2) -0.193(3) 0.2241(13) 0.042(6) Uani 1 1 d . U . . .
N4 N -0.387(3) 0.054(3) 0.2291(13) 0.047(7) Uani 1 1 d . . . . .
C1 C -0.366(3) -0.162(3) 0.0241(11) 0.020(5) Uani 1 1 d . U . . .
H1B H -0.3063 -0.0730 0.0139 0.025 Uiso 1 1 calc R U . . .
C2 C -0.372(2) -0.195(2) 0.0728(10) 0.016(5) Uani 1 1 d . U . . .
C3 C -0.468(3) -0.319(3) 0.0909(15) 0.043(8) Uani 1 1 d . U . . .
H3B H -0.4869 -0.3339 0.1250 0.052 Uiso 1 1 calc R U . . .
C4 C -0.533(3) -0.416(3) 0.0573(14) 0.035(7) Uani 1 1 d . . . . .
H4B H -0.5807 -0.5068 0.0673 0.042 Uiso 1 1 calc R U . . .
C5 C -0.530(3) -0.382(3) 0.0061(13) 0.032(7) Uani 1 1 d . U . . .
H5A H -0.5876 -0.4472 -0.0169 0.039 Uiso 1 1 calc R U . . .
C6 C -0.277(3) -0.083(3) 0.1104(11) 0.025(6) Uani 1 1 d . . . . .
C7 C -0.218(3) 0.202(3) 0.4226(11) 0.033(7) Uani 1 1 d . . . . .
H7A H -0.2607 0.1154 0.4370 0.039 Uiso 1 1 calc R U . . .
C8 C -0.168(3) 0.229(3) 0.3708(11) 0.034(8) Uani 1 1 d D . . . .
C9 C -0.088(4) 0.368(4) 0.3580(16) 0.051(9) Uani 1 1 d . U . . .
H9A H -0.0381 0.3906 0.3282 0.061 Uiso 1 1 calc R U . . .
C10 C -0.079(3) 0.470(3) 0.3862(16) 0.047(8) Uani 1 1 d . U . . .
H10A H -0.0341 0.5600 0.3753 0.057 Uiso 1 1 calc R U . . .
C11 C -0.138(4) 0.435(4) 0.4298(19) 0.065(11) Uani 1 1 d . U . . .
H11A H -0.1338 0.5069 0.4481 0.078 Uiso 1 1 calc R U . . .
C12 C -0.179(3) 0.126(3) 0.3407(10) 0.025(6) Uani 1 1 d D U . . .
C13 C 0.152(3) -0.132(3) 0.2079(11) 0.028(6) Uani 1 1 d . U . . .
H13A H 0.1024 -0.1128 0.2309 0.034 Uiso 1 1 calc R U . . .
C14 C 0.153(3) -0.098(3) 0.1573(11) 0.020(5) Uani 1 1 d . U . . .
C15 C 0.204(4) -0.149(4) 0.1228(13) 0.048(9) Uani 1 1 d . . . . .
H15A H 0.1874 -0.1470 0.0888 0.057 Uiso 1 1 calc R U . . .
C16 C 0.287(3) -0.205(4) 0.1411(17) 0.050(10) Uani 1 1 d . . . . .
H16A H 0.3357 -0.2280 0.1192 0.060 Uiso 1 1 calc R U . . .
C17 C 0.289(3) -0.222(3) 0.1928(14) 0.038(8) Uani 1 1 d . . . . .
H17A H 0.3419 -0.2583 0.2050 0.045 Uiso 1 1 calc R U . . .
C18 C 0.067(3) -0.032(3) 0.1407(13) 0.028(6) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O2 2.30(2) 2 ?
Sm1 O4 2.325(19) . ?
Sm1 O5 2.33(2) . ?
Sm1 O3 2.41(3) . ?
Sm1 O1 2.43(2) . ?
Sm1 O6 2.487(19) . ?
Sm1 O7 2.52(2) . ?
Sm1 O8 2.534(19) . ?
Sm1 N4 2.91(3) . ?
O1 C6 1.25(4) . ?
O2 C6 1.28(3) . ?
O2 Sm1 2.30(2) 6_554 ?
O2 H2B 0.8200 . ?
O3 C12 1.26(3) . ?
O4 C12 1.27(3) 6_554 ?
O5 C18 1.27(4) . ?
O6 C18 1.15(4) 2 ?
O7 N4 1.27(3) . ?
O8 N4 1.21(4) . ?
O9 N4 1.23(3) . ?
N1 C1 1.29(4) . ?
N1 C5 1.35(4) . ?
N2 C11 1.18(6) . ?
N2 C7 1.51(5) . ?
N3 C17 1.27(4) . ?
N3 C13 1.36(4) . ?
C1 C2 1.34(4) . ?
C1 H1B 0.9300 . ?
C2 C3 1.36(4) . ?
C2 C6 1.55(4) . ?
C3 C4 1.32(5) . ?
C3 H3B 0.9300 . ?
C4 C5 1.41(5) . ?
C4 H4B 0.9300 . ?
C5 H5A 0.9300 . ?
C7 C8 1.47(4) . ?
C7 H7A 0.9300 . ?
C8 C12 1.37(2) . ?
C8 C9 1.41(5) . ?
C9 C10 1.34(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.30(6) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O4 1.27(3) 2 ?
C13 C14 1.40(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.36(4) . ?
C14 C18 1.56(4) . ?
C15 C16 1.45(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.40(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 O6 1.15(4) 6_554 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Sm1 O4 158.6(7) 2 . ?
O2 Sm1 O5 82.6(7) 2 . ?
O4 Sm1 O5 82.5(8) . . ?
O2 Sm1 O3 100.3(8) 2 . ?
O4 Sm1 O3 82.7(9) . . ?
O5 Sm1 O3 143.0(8) . . ?
O2 Sm1 O1 83.5(8) 2 . ?
O4 Sm1 O1 107.0(8) . . ?
O5 Sm1 O1 74.0(7) . . ?
O3 Sm1 O1 143.0(8) . . ?
O2 Sm1 O6 82.6(7) 2 . ?
O4 Sm1 O6 78.0(7) . . ?
O5 Sm1 O6 70.4(7) . . ?
O3 Sm1 O6 73.4(8) . . ?
O1 Sm1 O6 143.0(7) . . ?
O2 Sm1 O7 77.7(7) 2 . ?
O4 Sm1 O7 123.0(7) . . ?
O5 Sm1 O7 141.9(8) . . ?
O3 Sm1 O7 73.2(8) . . ?
O1 Sm1 O7 71.7(8) . . ?
O6 Sm1 O7 137.1(8) . . ?
O2 Sm1 O8 127.2(7) 2 . ?
O4 Sm1 O8 74.1(7) . . ?
O5 Sm1 O8 132.8(7) . . ?
O3 Sm1 O8 74.1(8) . . ?
O1 Sm1 O8 74.6(7) . . ?
O6 Sm1 O8 139.2(7) . . ?
O7 Sm1 O8 50.0(6) . . ?
O2 Sm1 N4 103.3(8) 2 . ?
O4 Sm1 N4 97.6(8) . . ?
O5 Sm1 N4 145.9(9) . . ?
O3 Sm1 N4 69.8(8) . . ?
O1 Sm1 N4 73.5(8) . . ?
O6 Sm1 N4 143.2(8) . . ?
O7 Sm1 N4 25.7(7) . . ?
O8 Sm1 N4 24.5(8) . . ?
C6 O1 Sm1 127.1(18) . . ?
C6 O2 Sm1 153.2(18) . 6_554 ?
C6 O2 H2B 109.5 . . ?
Sm1 O2 H2B 44.9 6_554 . ?
C12 O3 Sm1 133.6(19) . . ?
C12 O4 Sm1 137.0(18) 6_554 . ?
C18 O5 Sm1 160.6(19) . . ?
C18 O6 Sm1 134(2) 2 . ?
N4 O7 Sm1 94.6(17) . . ?
N4 O8 Sm1 95.5(17) . . ?
C1 N1 C5 119(3) . . ?
C11 N2 C7 119(4) . . ?
C17 N3 C13 120(3) . . ?
O8 N4 O9 122(3) . . ?
O8 N4 O7 119(3) . . ?
O9 N4 O7 118(3) . . ?
O8 N4 Sm1 59.9(15) . . ?
O9 N4 Sm1 178(3) . . ?
O7 N4 Sm1 59.7(14) . . ?
N1 C1 C2 121(3) . . ?
N1 C1 H1B 119.5 . . ?
C2 C1 H1B 119.5 . . ?
C1 C2 C3 122(3) . . ?
C1 C2 C6 119(2) . . ?
C3 C2 C6 119(3) . . ?
C4 C3 C2 116(3) . . ?
C4 C3 H3B 122.0 . . ?
C2 C3 H3B 122.0 . . ?
C3 C4 C5 120(3) . . ?
C3 C4 H4B 119.9 . . ?
C5 C4 H4B 119.9 . . ?
N1 C5 C4 119(3) . . ?
N1 C5 H5A 120.6 . . ?
C4 C5 H5A 120.6 . . ?
O1 C6 O2 123(3) . . ?
O1 C6 C2 118(2) . . ?
O2 C6 C2 119(3) . . ?
C8 C7 N2 114(3) . . ?
C8 C7 H7A 123.2 . . ?
N2 C7 H7A 123.2 . . ?
C12 C8 C9 123(3) . . ?
C12 C8 C7 121(3) . . ?
C9 C8 C7 115(3) . . ?
C10 C9 C8 124(4) . . ?
C10 C9 H9A 118.2 . . ?
C8 C9 H9A 118.2 . . ?
C11 C10 C9 116(4) . . ?
C11 C10 H10A 122.0 . . ?
C9 C10 H10A 122.0 . . ?
N2 C11 C10 132(5) . . ?
N2 C11 H11A 114.2 . . ?
C10 C11 H11A 114.2 . . ?
O3 C12 O4 124(2) . 2 ?
O3 C12 C8 117(3) . . ?
O4 C12 C8 119(3) 2 . ?
N3 C13 C14 121(3) . . ?
N3 C13 H13A 119.4 . . ?
C14 C13 H13A 119.4 . . ?
C15 C14 C13 119(3) . . ?
C15 C14 C18 121(3) . . ?
C13 C14 C18 119(2) . . ?
C14 C15 C16 117(3) . . ?
C14 C15 H15A 121.3 . . ?
C16 C15 H15A 121.3 . . ?
C17 C16 C15 117(3) . . ?
C17 C16 H16A 121.3 . . ?
C15 C16 H16A 121.3 . . ?
N3 C17 C16 124(3) . . ?
N3 C17 H17A 118.2 . . ?
C16 C17 H17A 118.2 . . ?
O6 C18 O5 130(3) 6_554 . ?
O6 C18 C14 117(3) 6_554 . ?
O5 C18 C14 113(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Sm1 O8 N4 O9 179(3) . . . . ?
Sm1 O8 N4 O7 -9(3) . . . . ?
Sm1 O7 N4 O8 9(3) . . . . ?
Sm1 O7 N4 O9 -179(3) . . . . ?
C5 N1 C1 C2 1(4) . . . . ?
N1 C1 C2 C3 -8(4) . . . . ?
N1 C1 C2 C6 179(2) . . . . ?
C1 C2 C3 C4 16(4) . . . . ?
C6 C2 C3 C4 -171(3) . . . . ?
C2 C3 C4 C5 -17(4) . . . . ?
C1 N1 C5 C4 -3(4) . . . . ?
C3 C4 C5 N1 11(5) . . . . ?
Sm1 O1 C6 O2 -6(4) . . . . ?
Sm1 O1 C6 C2 170.9(16) . . . . ?
Sm1 O2 C6 O1 100(5) 6_554 . . . ?
Sm1 O2 C6 C2 -77(5) 6_554 . . . ?
C1 C2 C6 O1 173(2) . . . . ?
C3 C2 C6 O1 0(4) . . . . ?
C1 C2 C6 O2 -9(4) . . . . ?
C3 C2 C6 O2 177(3) . . . . ?
C11 N2 C7 C8 -2(6) . . . . ?
N2 C7 C8 C12 179(3) . . . . ?
N2 C7 C8 C9 10(4) . . . . ?
C12 C8 C9 C10 178(3) . . . . ?
C7 C8 C9 C10 -13(5) . . . . ?
C8 C9 C10 C11 7(6) . . . . ?
C7 N2 C11 C10 -5(9) . . . . ?
C9 C10 C11 N2 3(8) . . . . ?
Sm1 O3 C12 O4 6(4) . . . 2 ?
Sm1 O3 C12 C8 -172(2) . . . . ?
C9 C8 C12 O3 -12(5) . . . . ?
C7 C8 C12 O3 180(3) . . . . ?
C9 C8 C12 O4 170(3) . . . 2 ?
C7 C8 C12 O4 2(4) . . . 2 ?
C17 N3 C13 C14 -2(4) . . . . ?
N3 C13 C14 C15 12(4) . . . . ?
N3 C13 C14 C18 179(2) . . . . ?
C13 C14 C15 C16 -15(5) . . . . ?
C18 C14 C15 C16 178(3) . . . . ?
C14 C15 C16 C17 10(5) . . . . ?
C13 N3 C17 C16 -4(5) . . . . ?
C15 C16 C17 N3 0(5) . . . . ?
Sm1 O5 C18 O6 -33(8) . . . 6_554 ?
Sm1 O5 C18 C14 146(5) . . . . ?
C15 C14 C18 O6 -26(4) . . . 6_554 ?
C13 C14 C18 O6 168(3) . . . 6_554 ?
C15 C14 C18 O5 155(3) . . . . ?
C13 C14 C18 O5 -11(4) . . . . ?

_refine_diff_density_max         1.659
_refine_diff_density_min         -1.369
_refine_diff_density_rms         0.225

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 1516466'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N4 O9 Tb'
_chemical_formula_weight         588.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+5/6'
'-y, x-y, z+2/3'
'-x, -y, z+1/2'
'-x+y, -x, z+1/3'
'y, -x+y, z+1/6'

_cell_length_a                   11.2771(3)
_cell_length_b                   11.2771(3)
_cell_length_c                   26.6390(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2933.9(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4475
_cell_measurement_theta_min      2.085
_cell_measurement_theta_max      27.624

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.998
_exptl_crystal_F_000             1716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    3.678
_shelx_estimated_absorpt_T_min   0.426
_shelx_estimated_absorpt_T_max   0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_T_max  0.620
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17904
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.085
_diffrn_reflns_theta_max         27.624
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4475
_reflns_number_gt                4227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0308P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.004(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4475
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_ref         0.0528
_refine_ls_wR_factor_gt          0.0521
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb -0.85479(2) -0.82777(2) 0.13925(2) 0.01641(7) Uani 1 1 d . . . . .
O1 O -0.9987(4) -0.7598(5) 0.10551(17) 0.0298(10) Uani 1 1 d . . . . .
O2 O -1.1522(5) -0.8628(5) 0.04488(15) 0.0320(10) Uani 1 1 d . . . . .
O3 O -0.9829(5) -1.0178(4) 0.08905(15) 0.0341(10) Uani 1 1 d . . . . .
O4 O -1.0671(4) -0.9796(5) 0.18196(16) 0.0322(10) Uani 1 1 d . . . . .
O5 O -0.7078(4) -0.8132(5) 0.07099(15) 0.0309(10) Uani 1 1 d . . . . .
O6 O -0.7821(5) -0.9649(4) 0.17423(17) 0.0261(9) Uani 1 1 d . . . . .
H6A H -0.8505 -0.9770 0.1590 0.039 Uiso 1 1 calc R U . . .
O7 O -0.6113(5) -0.6644(5) 0.16406(18) 0.0339(10) Uani 1 1 d . . . . .
O8 O -0.7132(5) -0.5799(5) 0.12086(17) 0.0344(11) Uani 1 1 d . . . . .
O9 O -0.5088(6) -0.4459(5) 0.1497(3) 0.0632(17) Uani 1 1 d . . . . .
N1 N -1.4706(6) -0.9191(8) 0.1343(3) 0.059(2) Uani 1 1 d . . . . .
N2 N -1.2192(5) -1.4124(5) 0.1392(2) 0.0347(11) Uani 1 1 d . . . . .
N3 N -0.5558(5) -0.8127(6) -0.09369(19) 0.0328(12) Uani 1 1 d . . . . .
N4 N -0.6083(5) -0.5593(5) 0.1449(2) 0.0323(12) Uani 1 1 d . . . . .
C1 C -1.3645(7) -0.9020(8) 0.1072(3) 0.0407(17) Uani 1 1 d . . . . .
H1B H -1.3824 -0.9401 0.0752 0.049 Uiso 1 1 calc R U . . .
C2 C -1.2301(6) -0.8324(7) 0.1226(2) 0.0260(13) Uani 1 1 d . . . . .
C3 C -1.2049(7) -0.7812(7) 0.1712(2) 0.0319(14) Uani 1 1 d . . . . .
H3B H -1.1165 -0.7378 0.1843 0.038 Uiso 1 1 calc R U . . .
C4 C -1.3126(8) -0.7958(8) 0.1996(3) 0.0450(19) Uani 1 1 d . . . . .
H4B H -1.2980 -0.7609 0.2321 0.054 Uiso 1 1 calc R U . . .
C5 C -1.4416(8) -0.8620(9) 0.1799(3) 0.049(2) Uani 1 1 d . . . . .
H5A H -1.5130 -0.8678 0.1992 0.059 Uiso 1 1 calc R U . . .
C6 C -1.1179(6) -0.8180(6) 0.0883(2) 0.0231(12) Uani 1 1 d . . . . .
C7 C -1.1515(6) -1.2836(6) 0.1227(2) 0.0272(13) Uani 1 1 d . . . . .
H7A H -1.1064 -1.2138 0.1460 0.033 Uiso 1 1 calc R U . . .
C8 C -1.1450(6) -1.2484(6) 0.0726(2) 0.0239(12) Uani 1 1 d . . . . .
C9 C -1.2107(7) -1.3526(6) 0.0384(2) 0.0344(15) Uani 1 1 d . . . . .
H9A H -1.2082 -1.3332 0.0043 0.041 Uiso 1 1 calc R U . . .
C10 C -1.2805(8) -1.4861(7) 0.0551(3) 0.0462(18) Uani 1 1 d . . . . .
H10A H -1.3257 -1.5578 0.0324 0.055 Uiso 1 1 calc R U . . .
C11 C -1.2824(8) -1.5119(7) 0.1051(3) 0.0425(17) Uani 1 1 d . . . . .
H11A H -1.3296 -1.6023 0.1160 0.051 Uiso 1 1 calc R U . . .
C12 C -1.0662(6) -1.0985(6) 0.0574(2) 0.0232(12) Uani 1 1 d . . . . .
C13 C -0.6364(6) -0.7949(6) -0.0616(2) 0.0261(13) Uani 1 1 d . . . . .
H13A H -0.6965 -0.7675 -0.0735 0.031 Uiso 1 1 calc R U . . .
C14 C -0.6312(6) -0.8169(6) -0.0106(2) 0.0208(12) Uani 1 1 d . . . . .
C15 C -0.5379(7) -0.8535(7) 0.0061(2) 0.0329(15) Uani 1 1 d . . . . .
H15A H -0.5305 -0.8660 0.0403 0.040 Uiso 1 1 calc R U . . .
C16 C -0.4561(7) -0.8716(7) -0.0274(3) 0.0406(16) Uani 1 1 d . . . . .
H16A H -0.3944 -0.8978 -0.0164 0.049 Uiso 1 1 calc R U . . .
C17 C -0.4668(7) -0.8503(7) -0.0776(3) 0.0394(17) Uani 1 1 d . . . . .
H17A H -0.4117 -0.8622 -0.1007 0.047 Uiso 1 1 calc R U . . .
C18 C -0.7264(6) -0.8029(6) 0.0255(2) 0.0210(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O6 2.281(4) . ?
Tb1 O1 2.296(4) . ?
Tb1 O3 2.318(4) . ?
Tb1 O2 2.363(4) 6_545 ?
Tb1 O5 2.410(4) . ?
Tb1 O4 2.421(4) . ?
Tb1 O8 2.477(5) . ?
Tb1 O7 2.512(5) . ?
Tb1 N4 2.915(5) . ?
O1 C6 1.252(7) . ?
O2 C6 1.243(7) . ?
O2 Tb1 2.363(4) 2_454 ?
O3 C12 1.251(7) . ?
O4 C12 1.236(7) 6_545 ?
O5 C18 1.244(7) . ?
O6 C18 1.254(7) 6_545 ?
O6 H6A 0.8200 . ?
O7 N4 1.275(7) . ?
O8 N4 1.260(7) . ?
O9 N4 1.216(7) . ?
N1 C1 1.327(9) . ?
N1 C5 1.336(11) . ?
N2 C7 1.334(8) . ?
N2 C11 1.338(9) . ?
N3 C13 1.334(8) . ?
N3 C17 1.340(9) . ?
C1 C2 1.375(9) . ?
C1 H1B 0.9300 . ?
C2 C3 1.389(9) . ?
C2 C6 1.502(8) . ?
C3 C4 1.369(9) . ?
C3 H3B 0.9300 . ?
C4 C5 1.366(11) . ?
C4 H4B 0.9300 . ?
C5 H5A 0.9300 . ?
C7 C8 1.383(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.374(9) . ?
C8 C12 1.520(8) . ?
C9 C10 1.378(9) . ?
C9 H9A 0.9300 . ?
C10 C11 1.362(10) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O4 1.236(7) 2_454 ?
C13 C14 1.388(8) . ?
C13 H13A 0.9300 . ?
C14 C15 1.382(9) . ?
C14 C18 1.507(7) . ?
C15 C16 1.371(9) . ?
C15 H15A 0.9300 . ?
C16 C17 1.374(11) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 O6 1.254(7) 2_454 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Tb1 O1 160.05(16) . . ?
O6 Tb1 O3 82.98(16) . . ?
O1 Tb1 O3 82.24(17) . . ?
O6 Tb1 O2 99.98(16) . 6_545 ?
O1 Tb1 O2 84.36(16) . 6_545 ?
O3 Tb1 O2 143.80(17) . 6_545 ?
O6 Tb1 O5 83.46(15) . . ?
O1 Tb1 O5 105.00(15) . . ?
O3 Tb1 O5 73.57(16) . . ?
O2 Tb1 O5 142.57(16) 6_545 . ?
O6 Tb1 O4 83.80(16) . . ?
O1 Tb1 O4 78.80(15) . . ?
O3 Tb1 O4 71.23(15) . . ?
O2 Tb1 O4 73.24(16) 6_545 . ?
O5 Tb1 O4 143.71(16) . . ?
O6 Tb1 O8 126.76(16) . . ?
O1 Tb1 O8 73.17(16) . . ?
O3 Tb1 O8 132.94(15) . . ?
O2 Tb1 O8 73.36(16) 6_545 . ?
O5 Tb1 O8 74.97(16) . . ?
O4 Tb1 O8 137.95(16) . . ?
O6 Tb1 O7 76.00(16) . . ?
O1 Tb1 O7 123.64(16) . . ?
O3 Tb1 O7 141.00(17) . . ?
O2 Tb1 O7 73.07(16) 6_545 . ?
O5 Tb1 O7 71.71(15) . . ?
O4 Tb1 O7 136.63(15) . . ?
O8 Tb1 O7 51.19(14) . . ?
O6 Tb1 N4 101.76(15) . . ?
O1 Tb1 N4 98.03(16) . . ?
O3 Tb1 N4 145.06(16) . . ?
O2 Tb1 N4 70.16(16) 6_545 . ?
O5 Tb1 N4 72.66(16) . . ?
O4 Tb1 N4 143.39(16) . . ?
O8 Tb1 N4 25.40(15) . . ?
O7 Tb1 N4 25.83(15) . . ?
C6 O1 Tb1 136.2(4) . . ?
C6 O2 Tb1 133.2(4) . 2_454 ?
C12 O3 Tb1 162.8(4) . . ?
C12 O4 Tb1 135.3(4) 6_545 . ?
C18 O5 Tb1 126.7(4) . . ?
C18 O6 Tb1 152.4(4) 6_545 . ?
C18 O6 H6A 109.5 6_545 . ?
Tb1 O6 H6A 44.2 . . ?
N4 O7 Tb1 95.0(3) . . ?
N4 O8 Tb1 97.1(3) . . ?
C1 N1 C5 116.1(6) . . ?
C7 N2 C11 117.6(6) . . ?
C13 N3 C17 121.1(6) . . ?
O9 N4 O8 122.4(6) . . ?
O9 N4 O7 121.1(6) . . ?
O8 N4 O7 116.5(5) . . ?
O9 N4 Tb1 176.1(5) . . ?
O8 N4 Tb1 57.5(3) . . ?
O7 N4 Tb1 59.2(3) . . ?
N1 C1 C2 125.2(7) . . ?
N1 C1 H1B 117.4 . . ?
C2 C1 H1B 117.4 . . ?
C1 C2 C3 117.0(6) . . ?
C1 C2 C6 120.5(5) . . ?
C3 C2 C6 122.4(6) . . ?
C4 C3 C2 118.7(6) . . ?
C4 C3 H3B 120.6 . . ?
C2 C3 H3B 120.6 . . ?
C5 C4 C3 119.5(7) . . ?
C5 C4 H4B 120.3 . . ?
C3 C4 H4B 120.3 . . ?
N1 C5 C4 123.4(7) . . ?
N1 C5 H5A 118.3 . . ?
C4 C5 H5A 118.3 . . ?
O2 C6 O1 126.0(5) . . ?
O2 C6 C2 116.6(5) . . ?
O1 C6 C2 117.4(5) . . ?
N2 C7 C8 123.4(6) . . ?
N2 C7 H7A 118.3 . . ?
C8 C7 H7A 118.3 . . ?
C9 C8 C7 117.8(6) . . ?
C9 C8 C12 122.7(5) . . ?
C7 C8 C12 119.5(5) . . ?
C8 C9 C10 119.3(6) . . ?
C8 C9 H9A 120.3 . . ?
C10 C9 H9A 120.3 . . ?
C11 C10 C9 119.2(6) . . ?
C11 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
N2 C11 C10 122.7(6) . . ?
N2 C11 H11A 118.6 . . ?
C10 C11 H11A 118.6 . . ?
O4 C12 O3 125.9(6) 2_454 . ?
O4 C12 C8 118.1(5) 2_454 . ?
O3 C12 C8 116.0(5) . . ?
N3 C13 C14 120.6(6) . . ?
N3 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C15 C14 C13 118.4(5) . . ?
C15 C14 C18 121.0(5) . . ?
C13 C14 C18 120.7(5) . . ?
C16 C15 C14 120.2(6) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 119.0(6) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
N3 C17 C16 120.7(6) . . ?
N3 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
O5 C18 O6 125.5(5) . 2_454 ?
O5 C18 C14 116.7(5) . . ?
O6 C18 C14 117.8(5) 2_454 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Tb1 O8 N4 O9 -175.4(6) . . . . ?
Tb1 O8 N4 O7 4.7(6) . . . . ?
Tb1 O7 N4 O9 175.5(6) . . . . ?
Tb1 O7 N4 O8 -4.6(6) . . . . ?
C5 N1 C1 C2 0.6(13) . . . . ?
N1 C1 C2 C3 2.9(12) . . . . ?
N1 C1 C2 C6 -179.2(7) . . . . ?
C1 C2 C3 C4 -3.7(10) . . . . ?
C6 C2 C3 C4 178.5(6) . . . . ?
C2 C3 C4 C5 1.2(11) . . . . ?
C1 N1 C5 C4 -3.5(14) . . . . ?
C3 C4 C5 N1 2.6(14) . . . . ?
Tb1 O2 C6 O1 -4.7(10) 2_454 . . . ?
Tb1 O2 C6 C2 173.8(4) 2_454 . . . ?
Tb1 O1 C6 O2 -82.9(8) . . . . ?
Tb1 O1 C6 C2 98.6(6) . . . . ?
C1 C2 C6 O2 5.1(9) . . . . ?
C3 C2 C6 O2 -177.1(6) . . . . ?
C1 C2 C6 O1 -176.3(6) . . . . ?
C3 C2 C6 O1 1.6(9) . . . . ?
C11 N2 C7 C8 0.7(10) . . . . ?
N2 C7 C8 C9 -0.8(10) . . . . ?
N2 C7 C8 C12 179.5(6) . . . . ?
C7 C8 C9 C10 0.5(11) . . . . ?
C12 C8 C9 C10 -179.8(6) . . . . ?
C8 C9 C10 C11 -0.2(12) . . . . ?
C7 N2 C11 C10 -0.3(11) . . . . ?
C9 C10 C11 N2 0.1(13) . . . . ?
Tb1 O3 C12 O4 41.4(18) . . . 2_454 ?
Tb1 O3 C12 C8 -139.9(12) . . . . ?
C9 C8 C12 O4 16.8(9) . . . 2_454 ?
C7 C8 C12 O4 -163.4(6) . . . 2_454 ?
C9 C8 C12 O3 -161.9(6) . . . . ?
C7 C8 C12 O3 17.8(8) . . . . ?
C17 N3 C13 C14 -0.9(10) . . . . ?
N3 C13 C14 C15 1.9(9) . . . . ?
N3 C13 C14 C18 -177.3(6) . . . . ?
C13 C14 C15 C16 -2.0(9) . . . . ?
C18 C14 C15 C16 177.2(6) . . . . ?
C14 C15 C16 C17 1.2(11) . . . . ?
C13 N3 C17 C16 0.0(10) . . . . ?
C15 C16 C17 N3 -0.1(11) . . . . ?
Tb1 O5 C18 O6 8.9(9) . . . 2_454 ?
Tb1 O5 C18 C14 -171.1(4) . . . . ?
C15 C14 C18 O5 6.6(9) . . . . ?
C13 C14 C18 O5 -174.3(6) . . . . ?
C15 C14 C18 O6 -173.4(5) . . . 2_454 ?
C13 C14 C18 O6 5.7(9) . . . 2_454 ?

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.175

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8
_database_code_depnum_ccdc_archive 'CCDC 1516468'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Er N4 O9'
_chemical_formula_weight         596.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'

_cell_length_a                   11.2299(2)
_cell_length_b                   11.2299(2)
_cell_length_c                   26.4974(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2893.91(15)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4448
_cell_measurement_theta_min      3.116
_cell_measurement_theta_max      27.551

_exptl_crystal_description       block
_exptl_crystal_colour            golden
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.054
_exptl_crystal_F_000             1734
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    4.413
_shelx_estimated_absorpt_T_min   0.307
_shelx_estimated_absorpt_T_max   0.619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.507
_exptl_absorpt_correction_T_max  0.589
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45531
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.1264
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.116
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4448
_reflns_number_gt                4111
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4448
_refine_ls_number_parameters     290
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1329
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.061
_refine_ls_shift/su_mean         0.010

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Er1 Er -0.97370(5) -0.82761(5) -0.00210(3) 0.01709(18) Uani 1 1 d . . . . .
O1 O -0.9133(11) -0.9764(10) 0.0408(4) 0.030(2) Uani 1 1 d . . . . .
O2 O -1.0160(11) -1.0310(11) 0.1153(4) 0.036(2) Uani 1 1 d . . . . .
O3 O -0.7621(10) -0.7584(12) -0.0342(4) 0.030(2) Uani 1 1 d . . . . .
O4 O -0.8529(10) -0.7136(10) 0.0701(4) 0.028(2) Uani 1 1 d . . . . .
O5 O -1.1783(10) -0.9593(10) 0.0324(4) 0.029(2) Uani 1 1 d . . . . .
H5B H -1.2117 -0.9352 0.0098 0.035 Uiso 1 1 calc R U . . .
O6 O -1.1006(11) -0.8115(13) -0.0699(4) 0.036(3) Uani 1 1 d . . . . .
O7 O -0.8727(11) -0.5831(11) -0.0211(4) 0.032(2) Uani 1 1 d . . . . .
O8 O -1.0562(11) -0.6703(11) 0.0229(4) 0.033(2) Uani 1 1 d . . . . .
O9 O -0.9397(14) -0.4509(10) 0.0071(6) 0.054(4) Uani 1 1 d . . . . .
N1 N -0.7820(12) -1.1953(17) 0.1635(6) 0.044(3) Uani 1 1 d . . . . .
N2 N -0.4525(18) -0.920(2) -0.0081(7) 0.064(5) Uani 1 1 d . . . . .
N3 N -1.4473(14) -1.2572(15) -0.0682(5) 0.040(3) Uani 1 1 d . . . . .
N4 N -0.9499(13) -0.5580(14) 0.0037(5) 0.033(3) Uani 1 1 d . . . . .
C1 C -0.8470(13) -1.1308(15) 0.1469(5) 0.025(3) Uani 1 1 d . . . . .
H1B H -0.8887 -1.1033 0.1709 0.030 Uiso 1 1 calc R U . . .
C2 C -0.8575(12) -1.1016(13) 0.0976(5) 0.020(2) Uani 1 1 d . . . . .
C3 C -0.7968(18) -1.1420(16) 0.0626(6) 0.039(4) Uani 1 1 d . . . . .
H3B H -0.8041 -1.1268 0.0285 0.046 Uiso 1 1 calc R U . . .
C4 C -0.723(2) -1.206(2) 0.0774(7) 0.048(4) Uani 1 1 d . . . . .
H4B H -0.6801 -1.2332 0.0537 0.057 Uiso 1 1 calc R U . . .
C5 C -0.7165(17) -1.2295(19) 0.1292(6) 0.042(4) Uani 1 1 d . . . . .
H5A H -0.6655 -1.2694 0.1399 0.050 Uiso 1 1 calc R U . . .
C6 C -0.9410(15) -1.0348(13) 0.0831(5) 0.027(3) Uani 1 1 d . . . . .
C7 C -0.5389(16) -0.8987(17) -0.0351(6) 0.039(4) Uani 1 1 d . . . . .
H7A H -0.5555 -0.9322 -0.0680 0.047 Uiso 1 1 calc R U . . .
C8 C -0.6068(15) -0.8318(13) -0.0194(5) 0.023(3) Uani 1 1 d . . . . .
C9 C -0.5799(14) -0.7833(18) 0.0312(5) 0.035(4) Uani 1 1 d . . . . .
H9A H -0.6281 -0.7442 0.0454 0.043 Uiso 1 1 calc R U . . .
C10 C -0.4811(18) -0.794(2) 0.0595(7) 0.048(5) Uani 1 1 d . . . . .
H10A H -0.4591 -0.7588 0.0920 0.058 Uiso 1 1 calc R U . . .
C11 C -0.420(2) -0.856(2) 0.0394(7) 0.054(5) Uani 1 1 d . . . . .
H11A H -0.3503 -0.8577 0.0578 0.064 Uiso 1 1 calc R U . . .
C12 C -0.7040(12) -0.8160(14) -0.0534(5) 0.021(3) Uani 1 1 d . . . . .
C13 C -1.3648(13) -1.1589(14) -0.0366(5) 0.021(3) Uani 1 1 d . . . . .
H13A H -1.3031 -1.0715 -0.0487 0.025 Uiso 1 1 calc R U . . .
C14 C -1.3708(12) -1.1870(12) 0.0143(4) 0.016(2) Uani 1 1 d . U . . .
C15 C -1.4634(16) -1.3146(17) 0.0314(6) 0.041(4) Uani 1 1 d . . . . .
H15A H -1.4753 -1.3312 0.0659 0.049 Uiso 1 1 calc R U . . .
C16 C -1.5372(17) -1.4162(15) -0.0011(6) 0.038(3) Uani 1 1 d . . . . .
H16A H -1.5888 -1.5068 0.0098 0.046 Uiso 1 1 calc R U . . .
C17 C -1.5343(15) -1.3815(17) -0.0526(6) 0.037(4) Uani 1 1 d . . . . .
H17A H -1.5944 -1.4471 -0.0753 0.044 Uiso 1 1 calc R U . . .
C18 C -1.2711(13) -1.0741(13) 0.0508(5) 0.023(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Er1 O5 2.215(10) . ?
Er1 O3 2.265(9) . ?
Er1 O2 2.279(11) 6_544 ?
Er1 O4 2.324(9) . ?
Er1 O6 2.356(10) . ?
Er1 O1 2.383(10) . ?
Er1 O7 2.443(10) . ?
Er1 O8 2.460(10) . ?
Er1 N4 2.907(12) . ?
O1 C6 1.256(17) . ?
O2 C6 1.214(17) . ?
O2 Er1 2.279(11) 2_455 ?
O3 C12 1.235(17) . ?
O4 C12 1.231(16) 2_455 ?
O5 C18 1.281(16) . ?
O5 H5B 0.8200 . ?
O6 C18 1.247(15) 6_544 ?
O7 N4 1.228(16) . ?
O8 N4 1.329(17) . ?
O9 N4 1.154(16) . ?
N1 C1 1.334(18) . ?
N1 C5 1.34(2) . ?
N2 C7 1.32(2) . ?
N2 C11 1.40(3) . ?
N3 C17 1.31(2) . ?
N3 C13 1.326(17) . ?
C1 C2 1.366(19) . ?
C1 H1B 0.9300 . ?
C2 C3 1.36(2) . ?
C2 C6 1.515(19) . ?
C3 C4 1.40(2) . ?
C3 H3B 0.9300 . ?
C4 C5 1.40(2) . ?
C4 H4B 0.9300 . ?
C5 H5A 0.9300 . ?
C7 C8 1.38(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.421(18) . ?
C8 C12 1.493(18) . ?
C9 C10 1.40(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.31(3) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O4 1.231(16) 6_544 ?
C13 C14 1.378(19) . ?
C13 H13A 0.9300 . ?
C14 C15 1.360(19) . ?
C14 C18 1.541(17) . ?
C15 C16 1.33(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.42(3) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 O6 1.248(15) 2_455 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Er1 O3 160.8(4) . . ?
O5 Er1 O2 84.3(4) . 6_544 ?
O3 Er1 O2 82.2(4) . 6_544 ?
O5 Er1 O4 98.8(4) . . ?
O3 Er1 O4 84.1(4) . . ?
O2 Er1 O4 142.9(4) 6_544 . ?
O5 Er1 O6 84.3(4) . . ?
O3 Er1 O6 105.0(4) . . ?
O2 Er1 O6 74.5(4) 6_544 . ?
O4 Er1 O6 142.6(4) . . ?
O5 Er1 O1 84.2(4) . . ?
O3 Er1 O1 78.5(3) . . ?
O2 Er1 O1 70.9(4) 6_544 . ?
O4 Er1 O1 72.6(3) . . ?
O6 Er1 O1 144.4(4) . . ?
O5 Er1 O7 125.4(4) . . ?
O3 Er1 O7 73.7(4) . . ?
O2 Er1 O7 132.7(4) 6_544 . ?
O4 Er1 O7 74.7(3) . . ?
O6 Er1 O7 73.4(4) . . ?
O1 Er1 O7 138.8(4) . . ?
O5 Er1 O8 74.4(4) . . ?
O3 Er1 O8 124.2(4) . . ?
O2 Er1 O8 141.6(4) 6_544 . ?
O4 Er1 O8 73.1(4) . . ?
O6 Er1 O8 72.0(4) . . ?
O1 Er1 O8 135.8(3) . . ?
O7 Er1 O8 51.6(3) . . ?
O5 Er1 N4 101.4(4) . . ?
O3 Er1 N4 97.4(4) . . ?
O2 Er1 N4 145.9(4) 6_544 . ?
O4 Er1 N4 70.0(3) . . ?
O6 Er1 N4 72.8(4) . . ?
O1 Er1 N4 142.7(3) . . ?
O7 Er1 N4 24.6(4) . . ?
O8 Er1 N4 27.1(3) . . ?
C6 O1 Er1 135.0(9) . . ?
C6 O2 Er1 165.0(10) . 2_455 ?
C12 O3 Er1 135.5(10) . . ?
C12 O4 Er1 133.5(9) 2_455 . ?
C18 O5 Er1 151.5(10) . . ?
C18 O5 H5B 109.5 . . ?
Er1 O5 H5B 88.4 . . ?
C18 O6 Er1 128.4(8) 6_544 . ?
N4 O7 Er1 99.4(8) . . ?
N4 O8 Er1 95.5(7) . . ?
C1 N1 C5 117.3(14) . . ?
C7 N2 C11 114.8(15) . . ?
C17 N3 C13 121.7(13) . . ?
O9 N4 O7 124.6(15) . . ?
O9 N4 O8 122.2(13) . . ?
O7 N4 O8 112.9(11) . . ?
O9 N4 Er1 178.4(12) . . ?
O7 N4 Er1 56.0(7) . . ?
O8 N4 Er1 57.4(6) . . ?
N1 C1 C2 125.6(13) . . ?
N1 C1 H1B 117.2 . . ?
C2 C1 H1B 117.2 . . ?
C3 C2 C1 117.1(13) . . ?
C3 C2 C6 122.1(12) . . ?
C1 C2 C6 120.7(12) . . ?
C2 C3 C4 120.4(15) . . ?
C2 C3 H3B 119.8 . . ?
C4 C3 H3B 119.8 . . ?
C3 C4 C5 118.1(14) . . ?
C3 C4 H4B 121.0 . . ?
C5 C4 H4B 120.9 . . ?
N1 C5 C4 121.4(15) . . ?
N1 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
O2 C6 O1 127.2(14) . . ?
O2 C6 C2 116.7(12) . . ?
O1 C6 C2 115.5(12) . . ?
N2 C7 C8 126.4(15) . . ?
N2 C7 H7A 116.8 . . ?
C8 C7 H7A 116.8 . . ?
C7 C8 C9 115.2(13) . . ?
C7 C8 C12 121.3(12) . . ?
C9 C8 C12 123.5(13) . . ?
C10 C9 C8 119.9(16) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C11 C10 C9 118.6(17) . . ?
C11 C10 H10A 120.7 . . ?
C9 C10 H10A 120.7 . . ?
C10 C11 N2 124.5(15) . . ?
C10 C11 H11A 117.7 . . ?
N2 C11 H11A 117.7 . . ?
O3 C12 O4 129.4(12) . 6_544 ?
O3 C12 C8 114.9(11) . . ?
O4 C12 C8 115.7(12) 6_544 . ?
N3 C13 C14 119.6(13) . . ?
N3 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C13 C14 C15 119.5(12) . . ?
C13 C14 C18 119.5(11) . . ?
C15 C14 C18 121.0(12) . . ?
C16 C15 C14 120.4(15) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C17 117.8(14) . . ?
C15 C16 H16A 121.1 . . ?
C17 C16 H16A 121.1 . . ?
N3 C17 C16 120.1(13) . . ?
N3 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
O6 C18 O5 124.4(12) 2_455 . ?
O6 C18 C14 116.9(11) 2_455 . ?
O5 C18 C14 118.7(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Er1 O7 N4 O9 178.2(14) . . . . ?
Er1 O7 N4 O8 -7.7(12) . . . . ?
Er1 O8 N4 O9 -178.2(14) . . . . ?
Er1 O8 N4 O7 7.6(12) . . . . ?
C5 N1 C1 C2 3(2) . . . . ?
N1 C1 C2 C3 0(2) . . . . ?
N1 C1 C2 C6 176.5(14) . . . . ?
C1 C2 C3 C4 -2(2) . . . . ?
C6 C2 C3 C4 -178.4(15) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C1 N1 C5 C4 -4(3) . . . . ?
C3 C4 C5 N1 2(3) . . . . ?
Er1 O2 C6 O1 -20(5) 2_455 . . . ?
Er1 O2 C6 C2 151(3) 2_455 . . . ?
Er1 O1 C6 O2 2(2) . . . . ?
Er1 O1 C6 C2 -169.7(8) . . . . ?
C3 C2 C6 O2 163.7(14) . . . . ?
C1 C2 C6 O2 -12.4(19) . . . . ?
C3 C2 C6 O1 -24(2) . . . . ?
C1 C2 C6 O1 160.1(13) . . . . ?
C11 N2 C7 C8 -6(3) . . . . ?
N2 C7 C8 C9 -1(3) . . . . ?
N2 C7 C8 C12 -179.1(18) . . . . ?
C7 C8 C9 C10 6(2) . . . . ?
C12 C8 C9 C10 -176.0(15) . . . . ?
C8 C9 C10 C11 -3(3) . . . . ?
C9 C10 C11 N2 -4(4) . . . . ?
C7 N2 C11 C10 9(3) . . . . ?
Er1 O3 C12 O4 78.5(19) . . . 6_544 ?
Er1 O3 C12 C8 -102.4(13) . . . . ?
C7 C8 C12 O3 177.5(14) . . . . ?
C9 C8 C12 O3 -1(2) . . . . ?
C7 C8 C12 O4 -3.3(19) . . . 6_544 ?
C9 C8 C12 O4 178.4(13) . . . 6_544 ?
C17 N3 C13 C14 -1(2) . . . . ?
N3 C13 C14 C15 -1(2) . . . . ?
N3 C13 C14 C18 177.8(12) . . . . ?
C13 C14 C15 C16 7(2) . . . . ?
C18 C14 C15 C16 -171.7(15) . . . . ?
C14 C15 C16 C17 -11(3) . . . . ?
C13 N3 C17 C16 -3(2) . . . . ?
C15 C16 C17 N3 9(2) . . . . ?
Er1 O5 C18 O6 98(2) . . . 2_455 ?
Er1 O5 C18 C14 -83(2) . . . . ?
C13 C14 C18 O6 173.5(13) . . . 2_455 ?
C15 C14 C18 O6 -7(2) . . . 2_455 ?
C13 C14 C18 O5 -4.8(18) . . . . ?
C15 C14 C18 O5 174.3(13) . . . . ?

_refine_diff_density_max         2.037
_refine_diff_density_min         -2.035
_refine_diff_density_rms         0.206

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1516464'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Eu N4 O9'
_chemical_formula_weight         581.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+5/6'
'-y, x-y, z+2/3'
'-x, -y, z+1/2'
'-x+y, -x, z+1/3'
'y, -x+y, z+1/6'

_cell_length_a                   11.309(4)
_cell_length_b                   11.309(4)
_cell_length_c                   26.697(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2957(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4115
_cell_measurement_theta_min      2.079
_cell_measurement_theta_max      27.523

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.959
_exptl_crystal_F_000             1704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    3.244
_shelx_estimated_absorpt_T_min   0.396
_shelx_estimated_absorpt_T_max   0.678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.656
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15783
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.079
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4115
_reflns_number_gt                3923
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.989

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0783P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4115
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu -0.02684(4) -0.17116(4) 0.39543(3) 0.01661(14) Uani 1 1 d . . . . .
O1 O 0.1841(7) -0.0314(7) 0.3601(3) 0.0274(15) Uani 1 1 d . . . . .
H1A H 0.1670 -0.0931 0.3402 0.033 Uiso 1 1 calc R U . . .
O2 O 0.2944(8) 0.1092(8) 0.2970(3) 0.0308(17) Uani 1 1 d . . . . .
O3 O -0.0887(8) -0.0176(8) 0.3526(3) 0.0304(16) Uani 1 1 d . . . . .
O4 O 0.0364(9) 0.0211(8) 0.4457(3) 0.0360(18) Uani 1 1 d . . . . .
O5 O -0.1545(9) -0.2885(9) 0.3227(3) 0.0356(18) Uani 1 1 d . . . . .
O6 O -0.2402(7) -0.2390(9) 0.4293(3) 0.0307(16) Uani 1 1 d . . . . .
O7 O -0.1331(8) -0.4208(8) 0.4142(3) 0.0340(17) Uani 1 1 d . . . . .
O8 O 0.0517(8) -0.3363(8) 0.3704(3) 0.0320(16) Uani 1 1 d . . . . .
O9 O -0.0635(13) -0.5549(9) 0.3861(5) 0.064(3) Uani 1 1 d . . . . .
N1 N 0.4444(10) 0.2582(11) 0.4614(4) 0.035(2) Uani 1 1 d . . . . .
N2 N -0.2219(9) 0.1934(11) 0.2282(5) 0.037(2) Uani 1 1 d . . . . .
N3 N -0.4711(11) -0.5487(15) 0.2342(6) 0.063(4) Uani 1 1 d . . . . .
N4 N -0.0508(10) -0.4435(9) 0.3898(4) 0.034(2) Uani 1 1 d . . . . .
C1 C 0.3649(9) 0.1600(11) 0.4288(4) 0.026(2) Uani 1 1 d . . . . .
H1B H 0.3059 0.0721 0.4404 0.031 Uiso 1 1 calc R U . . .
C2 C 0.3697(10) 0.1874(10) 0.3790(4) 0.0218(18) Uani 1 1 d . . . . .
C3 C 0.4643(11) 0.3189(10) 0.3616(5) 0.032(2) Uani 1 1 d . . . . .
H3B H 0.4732 0.3387 0.3275 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5439(12) 0.4183(10) 0.3962(5) 0.039(2) Uani 1 1 d . . . . .
H4B H 0.6051 0.5067 0.3858 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5319(12) 0.3856(13) 0.4455(6) 0.041(3) Uani 1 1 d . . . . .
H5A H 0.5852 0.4524 0.4688 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2755(9) 0.0805(9) 0.3421(3) 0.0203(17) Uani 1 1 d . . . . .
C7 C -0.1523(12) 0.1315(13) 0.2453(4) 0.030(2) Uani 1 1 d . . . . .
H7A H -0.1068 0.1073 0.2221 0.036 Uiso 1 1 calc R U . . .
C8 C -0.1460(10) 0.1027(11) 0.2953(4) 0.0249(19) Uani 1 1 d . . . . .
C9 C -0.2115(14) 0.1433(14) 0.3295(5) 0.038(3) Uani 1 1 d . . . . .
H9A H -0.2070 0.1291 0.3636 0.045 Uiso 1 1 calc R U . . .
C10 C -0.2838(14) 0.2054(14) 0.3126(5) 0.043(3) Uani 1 1 d . . . . .
H10A H -0.3308 0.2305 0.3348 0.051 Uiso 1 1 calc R U . . .
C11 C -0.2833(14) 0.2284(14) 0.2616(5) 0.042(3) Uani 1 1 d . . . . .
H11A H -0.3298 0.2717 0.2504 0.050 Uiso 1 1 calc R U . . .
C12 C -0.0667(10) 0.0344(9) 0.3104(4) 0.0250(19) Uani 1 1 d . . . . .
C13 C -0.3679(12) -0.4617(13) 0.2606(5) 0.040(3) Uani 1 1 d . . . . .
H13A H -0.3864 -0.4404 0.2922 0.048 Uiso 1 1 calc R U . . .
C14 C -0.2324(10) -0.3977(10) 0.2458(4) 0.0229(19) Uani 1 1 d . . . . .
C15 C -0.2052(13) -0.4234(11) 0.1975(4) 0.033(2) Uani 1 1 d . . . . .
H15A H -0.1169 -0.3773 0.1846 0.039 Uiso 1 1 calc R U . . .
C16 C -0.3138(15) -0.5202(15) 0.1687(5) 0.046(3) Uani 1 1 d . . . . .
H16A H -0.2984 -0.5434 0.1369 0.055 Uiso 1 1 calc R U . . .
C17 C -0.4408(15) -0.5793(16) 0.1876(6) 0.056(4) Uani 1 1 d . . . . .
H17A H -0.5120 -0.6442 0.1682 0.067 Uiso 1 1 calc R U . . .
C18 C -0.1203(10) -0.3011(9) 0.2798(4) 0.0224(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O1 2.303(7) . ?
Eu1 O6 2.318(7) . ?
Eu1 O4 2.342(8) . ?
Eu1 O5 2.388(8) . ?
Eu1 O2 2.440(8) 6 ?
Eu1 O3 2.456(7) . ?
Eu1 O7 2.505(8) . ?
Eu1 O8 2.527(8) . ?
Eu1 N4 2.957(9) . ?
O1 C6 1.262(12) . ?
O1 H1A 0.8200 . ?
O2 C6 1.239(12) . ?
O2 Eu1 2.440(8) 2_554 ?
O3 C12 1.236(13) . ?
O4 C12 1.241(13) 6 ?
O5 C18 1.238(13) . ?
O6 C18 1.254(13) 6 ?
O7 N4 1.262(13) . ?
O8 N4 1.294(13) . ?
O9 N4 1.200(13) . ?
N1 C1 1.342(14) . ?
N1 C5 1.345(19) . ?
N2 C11 1.308(17) . ?
N2 C7 1.367(14) . ?
N3 C13 1.296(17) . ?
N3 C17 1.38(2) . ?
C1 C2 1.361(15) . ?
C1 H1B 0.9300 . ?
C2 C3 1.408(14) . ?
C2 C6 1.508(13) . ?
C3 C4 1.385(16) . ?
C3 H3B 0.9300 . ?
C4 C5 1.36(2) . ?
C4 H4B 0.9300 . ?
C5 H5A 0.9300 . ?
C7 C8 1.384(15) . ?
C7 H7A 0.9300 . ?
C8 C9 1.392(15) . ?
C8 C12 1.501(14) . ?
C9 C10 1.392(16) . ?
C9 H9A 0.9300 . ?
C10 C11 1.385(18) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O4 1.241(13) 2_554 ?
C13 C14 1.385(15) . ?
C13 H13A 0.9300 . ?
C14 C15 1.391(15) . ?
C14 C18 1.497(13) . ?
C15 C16 1.398(17) . ?
C15 H15A 0.9300 . ?
C16 C17 1.34(2) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 O6 1.254(13) 2_554 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Eu1 O6 159.4(3) . . ?
O1 Eu1 O4 82.4(3) . . ?
O6 Eu1 O4 82.4(3) . . ?
O1 Eu1 O5 100.3(3) . . ?
O6 Eu1 O5 83.9(3) . . ?
O4 Eu1 O5 143.3(3) . . ?
O1 Eu1 O2 83.1(3) . 6 ?
O6 Eu1 O2 105.8(3) . 6 ?
O4 Eu1 O2 73.9(3) . 6 ?
O5 Eu1 O2 142.8(3) . 6 ?
O1 Eu1 O3 83.5(3) . . ?
O6 Eu1 O3 78.4(3) . . ?
O4 Eu1 O3 71.0(3) . . ?
O5 Eu1 O3 73.0(3) . . ?
O2 Eu1 O3 143.7(3) 6 . ?
O1 Eu1 O7 127.1(3) . . ?
O6 Eu1 O7 73.5(3) . . ?
O4 Eu1 O7 133.1(3) . . ?
O5 Eu1 O7 73.8(3) . . ?
O2 Eu1 O7 74.9(3) 6 . ?
O3 Eu1 O7 138.1(3) . . ?
O1 Eu1 O8 76.9(3) . . ?
O6 Eu1 O8 123.4(3) . . ?
O4 Eu1 O8 141.3(3) . . ?
O5 Eu1 O8 73.3(3) . . ?
O2 Eu1 O8 71.5(3) 6 . ?
O3 Eu1 O8 136.9(3) . . ?
O7 Eu1 O8 50.8(3) . . ?
O1 Eu1 N4 102.6(3) . . ?
O6 Eu1 N4 97.9(3) . . ?
O4 Eu1 N4 145.3(3) . . ?
O5 Eu1 N4 70.4(3) . . ?
O2 Eu1 N4 72.7(3) 6 . ?
O3 Eu1 N4 143.4(3) . . ?
O7 Eu1 N4 25.0(3) . . ?
O8 Eu1 N4 25.8(3) . . ?
C6 O1 Eu1 153.1(7) . . ?
C6 O1 H1A 109.5 . . ?
Eu1 O1 H1A 87.7 . . ?
C6 O2 Eu1 125.9(6) . 2_554 ?
C12 O3 Eu1 134.4(7) . . ?
C12 O4 Eu1 162.7(8) 6 . ?
C18 O5 Eu1 132.7(7) . . ?
C18 O6 Eu1 136.3(7) 6 . ?
N4 O7 Eu1 98.0(6) . . ?
N4 O8 Eu1 96.0(6) . . ?
C1 N1 C5 120.7(10) . . ?
C11 N2 C7 117.1(11) . . ?
C13 N3 C17 116.0(11) . . ?
O9 N4 O7 122.9(11) . . ?
O9 N4 O8 122.1(11) . . ?
O7 N4 O8 115.0(8) . . ?
O9 N4 Eu1 177.7(10) . . ?
O7 N4 Eu1 57.0(5) . . ?
O8 N4 Eu1 58.2(5) . . ?
N1 C1 C2 120.7(10) . . ?
N1 C1 H1B 119.6 . . ?
C2 C1 H1B 119.6 . . ?
C1 C2 C3 119.1(10) . . ?
C1 C2 C6 121.5(9) . . ?
C3 C2 C6 119.4(9) . . ?
C4 C3 C2 118.6(11) . . ?
C4 C3 H3B 120.7 . . ?
C2 C3 H3B 120.7 . . ?
C5 C4 C3 119.5(11) . . ?
C5 C4 H4B 120.3 . . ?
C3 C4 H4B 120.3 . . ?
N1 C5 C4 121.3(10) . . ?
N1 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
O2 C6 O1 125.4(9) . . ?
O2 C6 C2 117.7(8) . . ?
O1 C6 C2 116.9(9) . . ?
N2 C7 C8 123.6(10) . . ?
N2 C7 H7A 118.2 . . ?
C8 C7 H7A 118.2 . . ?
C7 C8 C9 117.2(10) . . ?
C7 C8 C12 119.7(9) . . ?
C9 C8 C12 123.2(10) . . ?
C10 C9 C8 119.8(11) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C11 C10 C9 117.7(11) . . ?
C11 C10 H10A 121.1 . . ?
C9 C10 H10A 121.1 . . ?
N2 C11 C10 124.5(11) . . ?
N2 C11 H11A 117.7 . . ?
C10 C11 H11A 117.7 . . ?
O3 C12 O4 126.4(10) . 2_554 ?
O3 C12 C8 117.4(9) . . ?
O4 C12 C8 116.3(9) 2_554 . ?
N3 C13 C14 125.7(12) . . ?
N3 C13 H13A 117.2 . . ?
C14 C13 H13A 117.2 . . ?
C13 C14 C15 117.2(10) . . ?
C13 C14 C18 121.4(9) . . ?
C15 C14 C18 121.4(10) . . ?
C14 C15 C16 118.3(11) . . ?
C14 C15 H15A 120.8 . . ?
C16 C15 H15A 120.9 . . ?
C17 C16 C15 119.1(13) . . ?
C17 C16 H16A 120.5 . . ?
C15 C16 H16A 120.5 . . ?
C16 C17 N3 123.5(12) . . ?
C16 C17 H17A 118.3 . . ?
N3 C17 H17A 118.3 . . ?
O5 C18 O6 125.9(9) . 2_554 ?
O5 C18 C14 116.4(9) . . ?
O6 C18 C14 117.6(9) 2_554 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Eu1 O7 N4 O9 -177.3(12) . . . . ?
Eu1 O7 N4 O8 5.2(10) . . . . ?
Eu1 O8 N4 O9 177.3(12) . . . . ?
Eu1 O8 N4 O7 -5.1(10) . . . . ?
C5 N1 C1 C2 -0.9(17) . . . . ?
N1 C1 C2 C3 3.1(16) . . . . ?
N1 C1 C2 C6 -176.4(9) . . . . ?
C1 C2 C3 C4 -3.7(16) . . . . ?
C6 C2 C3 C4 175.9(10) . . . . ?
C2 C3 C4 C5 2.0(18) . . . . ?
C1 N1 C5 C4 -0.8(18) . . . . ?
C3 C4 C5 N1 0(2) . . . . ?
Eu1 O2 C6 O1 8.9(15) 2_554 . . . ?
Eu1 O2 C6 C2 -171.5(6) 2_554 . . . ?
Eu1 O1 C6 O2 -97.1(17) . . . . ?
Eu1 O1 C6 C2 83.4(17) . . . . ?
C1 C2 C6 O2 -173.5(10) . . . . ?
C3 C2 C6 O2 7.0(14) . . . . ?
C1 C2 C6 O1 6.1(14) . . . . ?
C3 C2 C6 O1 -173.4(9) . . . . ?
C11 N2 C7 C8 1.1(19) . . . . ?
N2 C7 C8 C9 -1.9(18) . . . . ?
N2 C7 C8 C12 -179.9(10) . . . . ?
C7 C8 C9 C10 2.4(19) . . . . ?
C12 C8 C9 C10 -179.6(11) . . . . ?
C8 C9 C10 C11 -2(2) . . . . ?
C7 N2 C11 C10 -1(2) . . . . ?
C9 C10 C11 N2 1(2) . . . . ?
Eu1 O3 C12 O4 -11.7(17) . . . 2_554 ?
Eu1 O3 C12 C8 168.6(7) . . . . ?
C7 C8 C12 O3 -163.7(10) . . . . ?
C9 C8 C12 O3 18.4(16) . . . . ?
C7 C8 C12 O4 16.6(14) . . . 2_554 ?
C9 C8 C12 O4 -161.4(11) . . . 2_554 ?
C17 N3 C13 C14 0(3) . . . . ?
N3 C13 C14 C15 4(2) . . . . ?
N3 C13 C14 C18 -178.4(14) . . . . ?
C13 C14 C15 C16 -5.4(17) . . . . ?
C18 C14 C15 C16 176.6(11) . . . . ?
C14 C15 C16 C17 3(2) . . . . ?
C15 C16 C17 N3 1(3) . . . . ?
C13 N3 C17 C16 -3(3) . . . . ?
Eu1 O5 C18 O6 -7.2(17) . . . 2_554 ?
Eu1 O5 C18 C14 173.2(7) . . . . ?
C13 C14 C18 O5 4.3(15) . . . . ?
C15 C14 C18 O5 -177.8(10) . . . . ?
C13 C14 C18 O6 -175.3(10) . . . 2_554 ?
C15 C14 C18 O6 2.6(15) . . . 2_554 ?

_refine_diff_density_max         0.979
_refine_diff_density_min         -2.100
_refine_diff_density_rms         0.374

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1516462'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N4 Nd O9'
_chemical_formula_weight         573.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+5/6'
'-y, x-y, z+2/3'
'-x, -y, z+1/2'
'-x+y, -x, z+1/3'
'y, -x+y, z+1/6'

_cell_length_a                   11.3285(3)
_cell_length_b                   11.3285(3)
_cell_length_c                   26.7591(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2974.0(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4544
_cell_measurement_theta_min      3.087
_cell_measurement_theta_max      27.507

_exptl_crystal_description       block
_exptl_crystal_colour            gray
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_F_000             1686
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.680
_shelx_estimated_absorpt_T_min   0.406
_shelx_estimated_absorpt_T_max   0.722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_T_max  0.706
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46059
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.087
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4544
_reflns_number_gt                4427
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+25.4263P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4544
_refine_ls_number_parameters     290
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 0.02583(5) -0.83179(6) 0.14223(4) 0.02178(16) Uani 1 1 d . . . . .
O1 O 0.1591(13) -0.7096(13) 0.0699(4) 0.050(3) Uani 1 1 d . . . . .
O2 O 0.0065(11) -0.7592(11) 0.0107(4) 0.044(3) Uani 1 1 d . . . . .
O3 O -0.0414(12) -1.0271(10) 0.1928(4) 0.043(2) Uani 1 1 d . . . . .
H3C H -0.1032 -1.0121 0.1997 0.051 Uiso 1 1 calc R U . . .
O4 O 0.0910(11) -0.9865(11) 0.0995(4) 0.040(2) Uani 1 1 d . . . . .
O5 O -0.1886(9) -0.9736(9) 0.1057(4) 0.032(2) Uani 1 1 d . . . . .
O6 O -0.1171(10) -0.8203(12) 0.2103(4) 0.040(2) Uani 1 1 d . . . . .
O7 O 0.1330(11) -0.5782(10) 0.1623(4) 0.039(2) Uani 1 1 d . . . . .
O8 O -0.0490(11) -0.6605(10) 0.1173(4) 0.042(2) Uani 1 1 d . . . . .
O9 O 0.0644(16) -0.4454(10) 0.1341(6) 0.072(4) Uani 1 1 d . . . . .
N1 N 0.4717(15) -0.4530(17) -0.0194(7) 0.069(4) Uani 1 1 d . U . . .
N2 N -0.1950(14) -1.4189(12) 0.1417(5) 0.045(3) Uani 1 1 d . . . . .
N3 N -0.4461(13) -1.2612(16) 0.2077(4) 0.044(3) Uani 1 1 d . . . . .
N4 N 0.0543(14) -0.5558(13) 0.1369(5) 0.042(3) Uani 1 1 d . . . . .
C1 C 0.3691(16) -0.5437(18) 0.0070(6) 0.050(4) Uani 1 1 d . . . . .
H1B H 0.3885 -0.5705 0.0373 0.061 Uiso 1 1 calc R U . . .
C2 C 0.2349(14) -0.6020(14) -0.0069(5) 0.031(3) Uani 1 1 d . . . . .
C3 C 0.2069(17) -0.5759(15) -0.0549(5) 0.042(3) Uani 1 1 d . . . . .
H3B H 0.1186 -0.6205 -0.0675 0.050 Uiso 1 1 calc R U . . .
C4 C 0.316(2) -0.4804(19) -0.0835(7) 0.055(4) Uani 1 1 d . . . . .
H4B H 0.3018 -0.4569 -0.1153 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4416(19) -0.423(2) -0.0646(7) 0.062(5) Uani 1 1 d . . . . .
H5A H 0.5130 -0.3587 -0.0839 0.075 Uiso 1 1 calc R U . . .
C6 C 0.1241(13) -0.6974(12) 0.0276(4) 0.030(3) Uani 1 1 d . U . . .
C7 C -0.1340(16) -1.2882(13) 0.1580(4) 0.033(3) Uani 1 1 d . . . . .
H7A H -0.1105 -1.2188 0.1348 0.040 Uiso 1 1 calc R U . . .
C8 C -0.1052(13) -1.2540(12) 0.2086(4) 0.027(2) Uani 1 1 d . . . . .
C9 C -0.1474(18) -1.3586(15) 0.2422(5) 0.045(4) Uani 1 1 d . . . . .
H9A H -0.1349 -1.3400 0.2763 0.054 Uiso 1 1 calc R U . . .
C10 C -0.2088(19) -1.4924(14) 0.2255(7) 0.050(4) Uani 1 1 d . . . . .
H10A H -0.2361 -1.5646 0.2477 0.061 Uiso 1 1 calc R U . . .
C11 C -0.2282(19) -1.5148(15) 0.1737(6) 0.049(4) Uani 1 1 d . . . . .
H11A H -0.2671 -1.6038 0.1620 0.058 Uiso 1 1 calc R U . . .
C12 C -0.0389(13) -1.1078(13) 0.2241(5) 0.031(2) Uani 1 1 d . . . . .
C13 C -0.3665(11) -1.1630(14) 0.1757(4) 0.027(2) Uani 1 1 d . . . . .
H13A H -0.3085 -1.0748 0.1871 0.032 Uiso 1 1 calc R U . . .
C14 C -0.3715(12) -1.1939(13) 0.1257(4) 0.025(2) Uani 1 1 d . . . . .
C15 C -0.4657(14) -1.3226(14) 0.1083(5) 0.037(3) Uani 1 1 d . . . . .
H15A H -0.4776 -1.3418 0.0743 0.045 Uiso 1 1 calc R U . . .
C16 C -0.5399(16) -1.4196(14) 0.1430(7) 0.046(3) Uani 1 1 d . . . . .
H16A H -0.5969 -1.5092 0.1329 0.055 Uiso 1 1 calc R U . . .
C17 C -0.5317(14) -1.3865(16) 0.1927(6) 0.043(4) Uani 1 1 d . . . . .
H17A H -0.5865 -1.4526 0.2158 0.052 Uiso 1 1 calc R U . . .
C18 C -0.2793(12) -1.0858(13) 0.0882(4) 0.025(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O5 2.352(9) . ?
Nd1 O2 2.356(10) 6_655 ?
Nd1 O3 2.370(10) . ?
Nd1 O1 2.420(10) . ?
Nd1 O6 2.483(10) . ?
Nd1 O4 2.494(10) . ?
Nd1 O7 2.555(10) . ?
Nd1 O8 2.564(10) . ?
Nd1 N4 2.981(12) . ?
O1 C6 1.229(17) . ?
O2 C6 1.239(17) . ?
O2 Nd1 2.356(10) 2_444 ?
O3 C12 1.251(16) . ?
O3 H3C 0.8200 . ?
O4 C12 1.240(17) 2_444 ?
O5 C18 1.259(16) . ?
O6 C18 1.234(15) 6_655 ?
O7 N4 1.245(17) . ?
O8 N4 1.289(17) . ?
O9 N4 1.200(16) . ?
N1 C1 1.31(2) . ?
N1 C5 1.34(3) . ?
N2 C11 1.28(2) . ?
N2 C7 1.356(17) . ?
N3 C17 1.32(2) . ?
N3 C13 1.334(17) . ?
C1 C2 1.37(2) . ?
C1 H1B 0.9300 . ?
C2 C3 1.390(19) . ?
C2 C6 1.495(17) . ?
C3 C4 1.40(2) . ?
C3 H3B 0.9300 . ?
C4 C5 1.33(3) . ?
C4 H4B 0.9300 . ?
C5 H5A 0.9300 . ?
C7 C8 1.402(17) . ?
C7 H7A 0.9300 . ?
C8 C9 1.368(18) . ?
C8 C12 1.494(18) . ?
C9 C10 1.39(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.41(2) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O4 1.240(17) 6_655 ?
C13 C14 1.377(17) . ?
C13 H13A 0.9300 . ?
C14 C15 1.387(17) . ?
C14 C18 1.522(16) . ?
C15 C16 1.36(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.37(2) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 O6 1.234(15) 2_444 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Nd1 O2 158.9(4) . 6_655 ?
O5 Nd1 O3 81.9(4) . . ?
O2 Nd1 O3 82.4(4) 6_655 . ?
O5 Nd1 O1 101.2(4) . . ?
O2 Nd1 O1 83.6(4) 6_655 . ?
O3 Nd1 O1 143.9(4) . . ?
O5 Nd1 O6 82.1(3) . . ?
O2 Nd1 O6 106.8(4) 6_655 . ?
O3 Nd1 O6 73.6(4) . . ?
O1 Nd1 O6 142.5(4) . . ?
O5 Nd1 O4 84.1(3) . . ?
O2 Nd1 O4 77.5(3) 6_655 . ?
O3 Nd1 O4 71.1(4) . . ?
O1 Nd1 O4 73.5(4) . . ?
O6 Nd1 O4 143.4(4) . . ?
O5 Nd1 O7 127.1(3) . . ?
O2 Nd1 O7 74.0(4) 6_655 . ?
O3 Nd1 O7 132.8(3) . . ?
O1 Nd1 O7 73.5(4) . . ?
O6 Nd1 O7 75.1(4) . . ?
O4 Nd1 O7 138.2(4) . . ?
O5 Nd1 O8 77.8(3) . . ?
O2 Nd1 O8 122.9(4) 6_655 . ?
O3 Nd1 O8 141.4(4) . . ?
O1 Nd1 O8 72.9(4) . . ?
O6 Nd1 O8 71.3(4) . . ?
O4 Nd1 O8 137.6(4) . . ?
O7 Nd1 O8 49.8(3) . . ?
O5 Nd1 N4 103.3(4) . . ?
O2 Nd1 N4 97.7(4) 6_655 . ?
O3 Nd1 N4 145.3(4) . . ?
O1 Nd1 N4 69.6(4) . . ?
O6 Nd1 N4 73.2(4) . . ?
O4 Nd1 N4 143.1(4) . . ?
O7 Nd1 N4 24.5(4) . . ?
O8 Nd1 N4 25.5(3) . . ?
C6 O1 Nd1 131.1(10) . . ?
C6 O2 Nd1 137.8(10) . 2_444 ?
C12 O3 Nd1 161.9(10) . . ?
C12 O3 H3C 109.5 . . ?
Nd1 O3 H3C 81.1 . . ?
C12 O4 Nd1 133.9(9) 2_444 . ?
C18 O5 Nd1 152.5(9) . . ?
C18 O6 Nd1 124.3(8) 6_655 . ?
N4 O7 Nd1 97.3(8) . . ?
N4 O8 Nd1 95.6(7) . . ?
C1 N1 C5 116.5(15) . . ?
C11 N2 C7 118.9(13) . . ?
C17 N3 C13 122.0(13) . . ?
O9 N4 O7 122.7(14) . . ?
O9 N4 O8 120.2(13) . . ?
O7 N4 O8 116.7(11) . . ?
O9 N4 Nd1 179.1(13) . . ?
O7 N4 Nd1 58.2(7) . . ?
O8 N4 Nd1 58.9(6) . . ?
N1 C1 C2 124.5(16) . . ?
N1 C1 H1B 117.7 . . ?
C2 C1 H1B 117.7 . . ?
C1 C2 C3 117.6(13) . . ?
C1 C2 C6 120.6(12) . . ?
C3 C2 C6 121.7(13) . . ?
C2 C3 C4 117.6(15) . . ?
C2 C3 H3B 121.2 . . ?
C4 C3 H3B 121.2 . . ?
C5 C4 C3 119.0(17) . . ?
C5 C4 H4B 120.5 . . ?
C3 C4 H4B 120.5 . . ?
C4 C5 N1 124.3(16) . . ?
C4 C5 H5A 117.9 . . ?
N1 C5 H5A 117.9 . . ?
O1 C6 O2 126.0(13) . . ?
O1 C6 C2 116.6(12) . . ?
O2 C6 C2 117.4(12) . . ?
N2 C7 C8 122.3(12) . . ?
N2 C7 H7A 118.8 . . ?
C8 C7 H7A 118.8 . . ?
C9 C8 C7 117.6(12) . . ?
C9 C8 C12 122.8(12) . . ?
C7 C8 C12 119.4(11) . . ?
C8 C9 C10 120.1(14) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C9 C10 C11 117.5(14) . . ?
C9 C10 H10A 121.2 . . ?
C11 C10 H10A 121.2 . . ?
N2 C11 C10 123.5(14) . . ?
N2 C11 H11A 118.2 . . ?
C10 C11 H11A 118.2 . . ?
O4 C12 O3 126.1(13) 6_655 . ?
O4 C12 C8 117.6(12) 6_655 . ?
O3 C12 C8 116.3(12) . . ?
N3 C13 C14 119.1(12) . . ?
N3 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C13 C14 C15 120.3(12) . . ?
C13 C14 C18 120.8(11) . . ?
C15 C14 C18 118.8(11) . . ?
C16 C15 C14 117.4(13) . . ?
C16 C15 H15A 121.3 . . ?
C14 C15 H15A 121.3 . . ?
C15 C16 C17 120.7(14) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
N3 C17 C16 120.1(12) . . ?
N3 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
O6 C18 O5 125.6(11) 2_444 . ?
O6 C18 C14 117.4(11) 2_444 . ?
O5 C18 C14 116.9(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Nd1 O7 N4 O9 -179.8(15) . . . . ?
Nd1 O7 N4 O8 7.3(13) . . . . ?
Nd1 O8 N4 O9 179.7(14) . . . . ?
Nd1 O8 N4 O7 -7.3(13) . . . . ?
C5 N1 C1 C2 -5(3) . . . . ?
N1 C1 C2 C3 8(3) . . . . ?
N1 C1 C2 C6 -175.6(18) . . . . ?
C1 C2 C3 C4 -7(2) . . . . ?
C6 C2 C3 C4 177.0(14) . . . . ?
C2 C3 C4 C5 3(3) . . . . ?
C3 C4 C5 N1 1(3) . . . . ?
C1 N1 C5 C4 0(4) . . . . ?
Nd1 O1 C6 O2 -8(2) . . . . ?
Nd1 O1 C6 C2 174.3(9) . . . . ?
Nd1 O2 C6 O1 -81.5(19) 2_444 . . . ?
Nd1 O2 C6 C2 96.6(16) 2_444 . . . ?
C1 C2 C6 O1 7(2) . . . . ?
C3 C2 C6 O1 -177.4(14) . . . . ?
C1 C2 C6 O2 -171.6(15) . . . . ?
C3 C2 C6 O2 4(2) . . . . ?
C11 N2 C7 C8 0(2) . . . . ?
N2 C7 C8 C9 -3(2) . . . . ?
N2 C7 C8 C12 -179.5(13) . . . . ?
C7 C8 C9 C10 4(2) . . . . ?
C12 C8 C9 C10 179.8(15) . . . . ?
C8 C9 C10 C11 -2(3) . . . . ?
C7 N2 C11 C10 2(3) . . . . ?
C9 C10 C11 N2 -2(3) . . . . ?
Nd1 O3 C12 O4 43(4) . . . 6_655 ?
Nd1 O3 C12 C8 -137(3) . . . . ?
C9 C8 C12 O4 21(2) . . . 6_655 ?
C7 C8 C12 O4 -163.6(13) . . . 6_655 ?
C9 C8 C12 O3 -159.7(15) . . . . ?
C7 C8 C12 O3 16.2(18) . . . . ?
C17 N3 C13 C14 -1(2) . . . . ?
N3 C13 C14 C15 5(2) . . . . ?
N3 C13 C14 C18 -178.2(12) . . . . ?
C13 C14 C15 C16 -8(2) . . . . ?
C18 C14 C15 C16 175.5(13) . . . . ?
C14 C15 C16 C17 7(2) . . . . ?
C13 N3 C17 C16 1(2) . . . . ?
C15 C16 C17 N3 -3(2) . . . . ?
Nd1 O5 C18 O6 -97(2) . . . 2_444 ?
Nd1 O5 C18 C14 81(2) . . . . ?
C13 C14 C18 O6 -174.1(12) . . . 2_444 ?
C15 C14 C18 O6 2.7(18) . . . 2_444 ?
C13 C14 C18 O5 8.3(18) . . . . ?
C15 C14 C18 O5 -174.9(12) . . . . ?

_refine_diff_density_max         1.457
_refine_diff_density_min         -1.104
_refine_diff_density_rms         0.139

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1516465'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Gd N4 O9'
_chemical_formula_weight         586.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'

_cell_length_a                   11.2815(2)
_cell_length_b                   11.2815(2)
_cell_length_c                   26.6752(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2940.17(15)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4492
_cell_measurement_theta_min      3.098
_cell_measurement_theta_max      27.469

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_F_000             1710
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    3.446
_shelx_estimated_absorpt_T_min   0.306
_shelx_estimated_absorpt_T_max   0.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.521
_exptl_absorpt_correction_T_max  0.617
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45464
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.098
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4492
_reflns_number_gt                4458
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)²+50.7788P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4492
_refine_ls_number_parameters     290
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1360
_refine_ls_wR_factor_gt          0.1357
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.82848(7) 0.85519(6) -0.00442(5) 0.01908(18) Uani 1 1 d . . . . .
O1 O 0.7112(13) 0.8625(15) 0.0682(4) 0.037(3) Uani 1 1 d . . . . .
O2 O 0.7604(12) 0.7608(14) 0.1285(5) 0.034(3) Uani 1 1 d . . . . .
O3 O 0.9792(13) 1.0690(12) 0.0388(4) 0.032(3) Uani 1 1 d . . . . .
O4 O 1.0209(12) 0.9846(13) -0.0547(5) 0.037(3) Uani 1 1 d . . . . .
H4A H 1.0430 1.0175 -0.0266 0.055 Uiso 1 1 calc R U . . .
O5 O 0.8148(14) 0.7066(13) -0.0727(4) 0.034(3) Uani 1 1 d . . . . .
O6 O 0.9667(12) 0.7841(13) 0.0309(5) 0.030(3) Uani 1 1 d . . . . .
O7 O 0.5811(12) 0.7117(13) -0.0238(4) 0.032(3) Uani 1 1 d . . . . .
O8 O 0.6643(13) 0.6117(13) 0.0205(5) 0.035(3) Uani 1 1 d . . . . .
O9 O 0.4471(13) 0.5093(16) 0.0042(7) 0.060(4) Uani 1 1 d . U . . .
N1 N 0.450(2) 0.919(2) 0.1562(9) 0.062(5) Uani 1 1 d . U . . .
N2 N 1.1945(17) 1.4156(14) 0.1621(6) 0.039(3) Uani 1 1 d . U . . .
N3 N 0.8135(18) 0.5564(16) -0.2369(5) 0.040(4) Uani 1 1 d . U . . .
N4 N 0.5563(16) 0.6084(15) 0.0015(6) 0.037(3) Uani 1 1 d . . . . .
C1 C 0.538(2) 0.904(2) 0.1303(7) 0.040(4) Uani 1 1 d . U . . .
H1B H 0.5604 0.9445 0.0988 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6032(18) 0.8328(17) 0.1447(6) 0.028(3) Uani 1 1 d . . . . .
C3 C 0.5777(17) 0.781(2) 0.1940(6) 0.035(4) Uani 1 1 d . . . . .
H3B H 0.6243 0.7399 0.2073 0.042 Uiso 1 1 calc R U . . .
C4 C 0.481(2) 0.794(2) 0.2226(8) 0.047(5) Uani 1 1 d . . . . .
H4B H 0.4595 0.7578 0.2548 0.057 Uiso 1 1 calc R U . . .
C5 C 0.420(2) 0.859(3) 0.2031(9) 0.053(6) Uani 1 1 d . U . . .
H5A H 0.3536 0.8638 0.2222 0.064 Uiso 1 1 calc R U . . .
C6 C 0.7007(15) 0.8167(16) 0.1110(5) 0.024(3) Uani 1 1 d . . . . .
C7 C 1.1302(19) 1.2838(16) 0.1459(6) 0.029(3) Uani 1 1 d . U . . .
H7A H 1.1037 1.2144 0.1695 0.035 Uiso 1 1 calc R U . . .
C8 C 1.1022(15) 1.2481(16) 0.0958(6) 0.024(3) Uani 1 1 d . . . . .
C9 C 1.144(2) 1.352(2) 0.0607(7) 0.043(5) Uani 1 1 d . . . . .
H9A H 1.1316 1.3317 0.0267 0.051 Uiso 1 1 calc R U . . .
C10 C 1.206(2) 1.4885(17) 0.0778(7) 0.038(4) Uani 1 1 d . U . . .
H10A H 1.2323 1.5608 0.0555 0.046 Uiso 1 1 calc R U . . .
C11 C 1.226(2) 1.511(2) 0.1297(8) 0.045(5) Uani 1 1 d . . . . .
H11A H 1.2649 1.6006 0.1413 0.054 Uiso 1 1 calc R U . . .
C12 C 1.0327(16) 1.1009(17) 0.0804(6) 0.027(3) Uani 1 1 d . . . . .
C13 C 0.7950(15) 0.6359(15) -0.2046(5) 0.022(3) Uani 1 1 d . U . . .
H13A H 0.7656 0.6949 -0.2160 0.026 Uiso 1 1 calc R U . . .
C14 C 0.8195(15) 0.6302(14) -0.1547(5) 0.021(3) Uani 1 1 d . . . . .
C15 C 0.853(2) 0.5351(18) -0.1365(7) 0.034(4) Uani 1 1 d . . . . .
H15A H 0.8585 0.5228 -0.1023 0.041 Uiso 1 1 calc R U . . .
C16 C 0.878(2) 0.4609(19) -0.1709(8) 0.040(4) Uani 1 1 d . . . . .
H16A H 0.9125 0.4050 -0.1606 0.048 Uiso 1 1 calc R U . . .
C17 C 0.853(2) 0.469(2) -0.2211(8) 0.042(5) Uani 1 1 d . . . . .
H17A H 0.8630 0.4126 -0.2442 0.050 Uiso 1 1 calc R U . . .
C18 C 0.8040(15) 0.7261(14) -0.1180(5) 0.019(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O6 2.284(12) . ?
Gd1 O2 2.308(12) 6_564 ?
Gd1 O4 2.340(12) . ?
Gd1 O1 2.370(11) . ?
Gd1 O5 2.427(11) . ?
Gd1 O3 2.437(12) . ?
Gd1 O7 2.481(12) . ?
Gd1 O8 2.516(12) . ?
Gd1 N4 2.942(15) . ?
O1 C6 1.236(19) . ?
O2 C6 1.22(2) . ?
O2 Gd1 2.308(12) 2_655 ?
O3 C12 1.23(2) . ?
O4 C12 1.25(2) 6_564 ?
O4 H4A 0.8200 . ?
O5 C18 1.245(17) . ?
O6 C18 1.251(18) 2_655 ?
O7 N4 1.25(2) . ?
O8 N4 1.30(2) . ?
O9 N4 1.18(2) . ?
N1 C1 1.30(3) . ?
N1 C5 1.38(3) . ?
N2 C11 1.28(3) . ?
N2 C7 1.36(2) . ?
N3 C13 1.33(2) . ?
N3 C17 1.34(3) . ?
C1 C2 1.38(3) . ?
C1 H1B 0.9300 . ?
C2 C3 1.41(2) . ?
C2 C6 1.50(2) . ?
C3 C4 1.39(3) . ?
C3 H3B 0.9300 . ?
C4 C5 1.34(3) . ?
C4 H4B 0.9300 . ?
C5 H5A 0.9300 . ?
C7 C8 1.38(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.38(2) . ?
C8 C12 1.50(2) . ?
C9 C10 1.41(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.41(3) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O4 1.25(2) 2_655 ?
C13 C14 1.37(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.39(2) . ?
C14 C18 1.53(2) . ?
C15 C16 1.36(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.38(3) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 O6 1.251(18) 6_564 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Gd1 O2 159.5(5) . 6_564 ?
O6 Gd1 O4 82.7(5) . . ?
O2 Gd1 O4 82.3(5) 6_564 . ?
O6 Gd1 O1 99.6(4) . . ?
O2 Gd1 O1 84.6(5) 6_564 . ?
O4 Gd1 O1 143.8(5) . . ?
O6 Gd1 O5 83.5(4) . . ?
O2 Gd1 O5 105.5(4) 6_564 . ?
O4 Gd1 O5 73.7(5) . . ?
O1 Gd1 O5 142.5(5) . . ?
O6 Gd1 O3 83.7(4) . . ?
O2 Gd1 O3 78.3(4) 6_564 . ?
O4 Gd1 O3 71.5(4) . . ?
O1 Gd1 O3 72.8(5) . . ?
O5 Gd1 O3 144.2(5) . . ?
O6 Gd1 O7 126.8(4) . . ?
O2 Gd1 O7 73.7(5) 6_564 . ?
O4 Gd1 O7 132.6(4) . . ?
O1 Gd1 O7 74.2(4) . . ?
O5 Gd1 O7 74.4(4) . . ?
O3 Gd1 O7 138.2(4) . . ?
O6 Gd1 O8 76.5(4) . . ?
O2 Gd1 O8 123.6(5) 6_564 . ?
O4 Gd1 O8 141.2(5) . . ?
O1 Gd1 O8 72.7(5) . . ?
O5 Gd1 O8 71.7(4) . . ?
O3 Gd1 O8 136.4(4) . . ?
O7 Gd1 O8 50.9(4) . . ?
O6 Gd1 N4 102.6(5) . . ?
O2 Gd1 N4 97.7(5) 6_564 . ?
O4 Gd1 N4 145.6(5) . . ?
O1 Gd1 N4 69.7(5) . . ?
O5 Gd1 N4 73.2(4) . . ?
O3 Gd1 N4 142.5(4) . . ?
O7 Gd1 N4 24.9(4) . . ?
O8 Gd1 N4 26.1(4) . . ?
C6 O1 Gd1 132.8(11) . . ?
C6 O2 Gd1 136.8(11) . 2_655 ?
C12 O3 Gd1 135.7(11) . . ?
C12 O4 Gd1 162.1(12) 6_564 . ?
C12 O4 H4A 109.5 6_564 . ?
Gd1 O4 H4A 74.6 . . ?
C18 O5 Gd1 125.8(10) . . ?
C18 O6 Gd1 153.2(11) 2_655 . ?
N4 O7 Gd1 98.6(10) . . ?
N4 O8 Gd1 95.5(9) . . ?
C1 N1 C5 115.6(19) . . ?
C11 N2 C7 118.5(16) . . ?
C13 N3 C17 121.0(15) . . ?
O9 N4 O7 123.8(17) . . ?
O9 N4 O8 121.4(16) . . ?
O7 N4 O8 114.4(13) . . ?
O9 N4 Gd1 179.6(15) . . ?
O7 N4 Gd1 56.5(8) . . ?
O8 N4 Gd1 58.4(8) . . ?
N1 C1 C2 126.4(19) . . ?
N1 C1 H1B 116.8 . . ?
C2 C1 H1B 116.8 . . ?
C1 C2 C3 116.2(16) . . ?
C1 C2 C6 122.3(15) . . ?
C3 C2 C6 121.4(16) . . ?
C4 C3 C2 118.5(18) . . ?
C4 C3 H3B 120.7 . . ?
C2 C3 H3B 120.7 . . ?
C5 C4 C3 119(2) . . ?
C5 C4 H4B 120.5 . . ?
C3 C4 H4B 120.5 . . ?
C4 C5 N1 123.9(19) . . ?
C4 C5 H5A 118.1 . . ?
N1 C5 H5A 118.1 . . ?
O2 C6 O1 127.4(15) . . ?
O2 C6 C2 117.4(14) . . ?
O1 C6 C2 115.2(14) . . ?
N2 C7 C8 123.0(15) . . ?
N2 C7 H7A 118.5 . . ?
C8 C7 H7A 118.5 . . ?
C9 C8 C7 118.3(16) . . ?
C9 C8 C12 121.3(15) . . ?
C7 C8 C12 120.3(14) . . ?
C8 C9 C10 118.6(17) . . ?
C8 C9 H9A 120.7 . . ?
C10 C9 H9A 120.7 . . ?
C11 C10 C9 117.5(16) . . ?
C11 C10 H10A 121.3 . . ?
C9 C10 H10A 121.3 . . ?
N2 C11 C10 123.9(17) . . ?
N2 C11 H11A 118.0 . . ?
C10 C11 H11A 118.0 . . ?
O3 C12 O4 125.8(16) . 2_655 ?
O3 C12 C8 118.8(15) . . ?
O4 C12 C8 115.4(14) 2_655 . ?
N3 C13 C14 119.6(15) . . ?
N3 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C13 C14 C15 121.0(15) . . ?
C13 C14 C18 119.4(13) . . ?
C15 C14 C18 119.5(13) . . ?
C16 C15 C14 117.3(16) . . ?
C16 C15 H15A 121.3 . . ?
C14 C15 H15A 121.3 . . ?
C15 C16 C17 119.9(17) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
N3 C17 C16 120.6(15) . . ?
N3 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
O5 C18 O6 125.9(14) . 6_564 ?
O5 C18 C14 116.1(12) . . ?
O6 C18 C14 118.1(12) 6_564 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Gd1 O7 N4 O9 179.6(17) . . . . ?
Gd1 O7 N4 O8 -7.8(15) . . . . ?
Gd1 O8 N4 O9 -179.6(17) . . . . ?
Gd1 O8 N4 O7 7.6(15) . . . . ?
C5 N1 C1 C2 1(4) . . . . ?
N1 C1 C2 C3 -5(3) . . . . ?
N1 C1 C2 C6 178(2) . . . . ?
C1 C2 C3 C4 6(3) . . . . ?
C6 C2 C3 C4 -177.0(18) . . . . ?
C2 C3 C4 C5 -3(3) . . . . ?
C3 C4 C5 N1 -2(4) . . . . ?
C1 N1 C5 C4 3(4) . . . . ?
Gd1 O2 C6 O1 81(2) 2_655 . . . ?
Gd1 O2 C6 C2 -99.0(18) 2_655 . . . ?
Gd1 O1 C6 O2 6(3) . . . . ?
Gd1 O1 C6 C2 -174.1(11) . . . . ?
C1 C2 C6 O2 174.7(17) . . . . ?
C3 C2 C6 O2 -2(2) . . . . ?
C1 C2 C6 O1 -5(2) . . . . ?
C3 C2 C6 O1 178.0(16) . . . . ?
C11 N2 C7 C8 3(3) . . . . ?
N2 C7 C8 C9 1(3) . . . . ?
N2 C7 C8 C12 179.1(16) . . . . ?
C7 C8 C9 C10 -4(3) . . . . ?
C12 C8 C9 C10 178.4(17) . . . . ?
C8 C9 C10 C11 2(3) . . . . ?
C7 N2 C11 C10 -4(3) . . . . ?
C9 C10 C11 N2 2(3) . . . . ?
Gd1 O3 C12 O4 11(3) . . . 2_655 ?
Gd1 O3 C12 C8 -170.0(11) . . . . ?
C9 C8 C12 O3 -20(3) . . . . ?
C7 C8 C12 O3 162.3(16) . . . . ?
C9 C8 C12 O4 159.5(18) . . . 2_655 ?
C7 C8 C12 O4 -18(2) . . . 2_655 ?
C17 N3 C13 C14 2(3) . . . . ?
N3 C13 C14 C15 -5(2) . . . . ?
N3 C13 C14 C18 177.4(14) . . . . ?
C13 C14 C15 C16 8(3) . . . . ?
C18 C14 C15 C16 -174.1(16) . . . . ?
C14 C15 C16 C17 -8(3) . . . . ?
C13 N3 C17 C16 -2(3) . . . . ?
C15 C16 C17 N3 5(3) . . . . ?
Gd1 O5 C18 O6 -8(2) . . . 6_564 ?
Gd1 O5 C18 C14 170.8(9) . . . . ?
C13 C14 C18 O5 173.3(14) . . . . ?
C15 C14 C18 O5 -4(2) . . . . ?
C13 C14 C18 O6 -8(2) . . . 6_564 ?
C15 C14 C18 O6 174.6(15) . . . 6_564 ?

_refine_diff_density_max         1.780
_refine_diff_density_min         -1.476
_refine_diff_density_rms         0.194

